تفاعل #42383

ord-b39dd9b74d0445a48965b470e709adbe

معادلة التفاعل

N#Cc1ccc2c(c1)CNCC2
1,2,3,4-tetrahydroisoquinoline-7-carbonitrile
CCN(CC)CC
triethylamine
CCCCBr
bromobutane
CCCCN1CCc2ccc(C#N)cc2C1
title compound
CCCCN1CCc2ccc(C#N)cc2C1
2-Butyl-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلwashed with water, and brine
  2. 2
    تجفيفdried (magnesium sulfate)
  3. 3
    ترشيحfiltered
  4. 4
    تركيزconcentrated under reduced pressure
  5. 5
    أخرىPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

الإجراء التجريبي

To an ice-cold, stirred solution of 1,2,3,4-tetrahydroisoquinoline-7-carbonitrile (J. Med. Chem. 1997, 40, 3997) (485 mg, 3.1 mmol) and triethylamine (0.47 mL, 3.4 mmol) in methylene chloride (5 mL) is added DMAP (37 mg, 0.3 mmol) and bromobutane (0.5 mL, 4.6 mmol). The reaction mixture is stirred for 20 h, diluted with methylene chloride, washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. ESI MS m/z 215 [M+H]+.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07727997B2uspto-grants-2010_06