تفاعل #2358507

ord-8aa796993bb040b49b22366bcc4bfcf0

معادلة التفاعل

CS(=O)(=O)c1cc(F)cc(OCCBr)c1
1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene
CCCN
propan-1-amine
CCCNCCOc1cc(F)cc(S(C)(=O)=O)c1
title compound
المردود 87.3%
CCCNCCOc1cc(F)cc(S(C)(=O)=O)c1
N-[2-(3-fluoro-5-methylsulfonyl-phenoxy)ethyl]propan-1-amine
المردود 87.3%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
120°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction mixtures
  2. 2
    درجة الحرارةwere cooled to room temperature
  3. 3
    ترشيحfiltrated
  4. 4
    أخرىwere evaporated
  5. 5
    أخرىPurification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1)

الإجراء التجريبي

A mixture of 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (2.65 g, 8.9 mmol) and propan-1-amine (5.24 ml, 63.7 mmol) in ethanol (32 ml) was divided into 3 aliquots which were each heated under microwave radiation at 120° C. for 30 min. The reaction mixtures were cooled to room temperature, filtrated and pooled before the volatiles were evaporated. Purification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (2.14 g, 87%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 191° C. MS m/z (relative intensity, 70 eV) 275 (M+, 2), 246 (32), 73 (5), 72 (bp), 56 (11).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09120728B2uspto-grants-2015_09