تفاعل #2075689

ord-b179739b4c5f49bf907ded43f7306c73

معادلة التفاعل

N
ammonia
CNC.Cl
dimethylamine hydrochloride
CCCCC/C=C\C/C=C\CCCCCCCCOc1ccc(C=O)cc1OCCCCCCCC/C=C\C/C=C\CCCCC
3,4-dilinoleyloxybenzaldehyde
[BH4-].[Na+]
Sodium borohydride
CCCCC/C=C\C/C=C\CCCCCCCCOc1ccc(CN(C)C)cc1OCCCCCCCC/C=C\C/C=C\CCCCC
yellow oil
المردود 74.4%
CCCCC/C=C\C/C=C\CCCCCCCCOc1ccc(CN(C)C)cc1OCCCCCCCC/C=C\C/C=C\CCCCC
N,N-Dimethyl-3,4-dilinoleyloxybenzylamine
المردود 74.4%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGto stir at room temperature overnight
  2. 2
    ترشيحThe reaction mixture was filtered
  3. 3
    تجفيفThe filtrate was dried over K2CO3
  4. 4
    ترشيحfiltered
  5. 5
    تركيزconcentrated
  6. 6
    أخرىThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)

الإجراء التجريبي

To a solution of triethylamineamine (2.0 mL, 14 mmol) in ethanol (20 mL) was added dimethylamine hydrochloride (1.63 g, 20 mmol), titanium tetraisopropoxide (5.96 mL, 20 mmol) and 3,4-dilinoleyloxybenzaldehyde (6.35 g, 10 mmol). The mixture was allowed to stir under argon for 10 h at room temperature. Sodium borohydride (0.57 g, 15 mmol) was added to the reaction mixture which was then allowed to stir at room temperature overnight. 6N Aqueous ammonia (30 mL), was added slowly to the reaction mixture followed by dichloromethane. The reaction mixture was filtered. The filtrate was dried over K2CO3, filtered and concentrated. The resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient) to afford 4.94 g (74%) of a yellow oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07641915B2uspto-grants-2010_01