1-Bromo-3-chloropropane → N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide

HRID 403130노트

반응식

HRID 403130 반응식
[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])OC(C)(C)C)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][N:9]([CH2:25][CH2:26][CH2:27][Cl:28])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

생성물 1

HCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide수율 55%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Compound 14 (1 g, 4.1 mmol), 1-bromo-3-chloropropane (9.7 g, 60 mmol) and K2CO3 (0.56 g, 4.09 mmol) were added to 50 mL CH3CN, and the solution was stirred for 48 h. The solvent was evaporated to dryness and the residue was purified on a silica gel TLC plate that was developed in 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 yield the desired product as a pale yellow oil (55%). 1H NMR (CDCl3) δ 7.341 (d, 1H, Ar), 7.139 (dd, 1H, Ar), 7.029 (m, 1H, Ar), 6.995 (m, 1H, Ar), 3.592 (s, 2H, —CH2—), 3.539 (t, 2H, —CH2—), 3.167 (m, 2H, —CH2—), 2.583 (ddd, 2H, —CH2—), 2.519 (ddd, 2H, —CH2—), 1.900 (p, 2H, —CH2—), 1.425 (s, 9H, —C(CH3)3), 1.385 (s, 9H, —C(CH3)3). Mass Spec.=399.96 (M+H)+.

후처리

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified on a silica gel TLC plate that

출처 및 근거

ORD 기록
ord-e0053acbb5fc43889d63d0b42d38387f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747810B2

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