1-Bromo-3-chloropropane → N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403125노트

반응식

HRID 403125 반응식
[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][Cl:25].C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:22][CH2:23][CH2:24][Cl:25])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896659N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamine

생성물 1

HCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

실험 절차

Compound 19 was synthesized with 9 (0.9 g, 3.32 mmol), using 1-bromo-3-chloropropane (10.5 g, 66 mmol) and K2CO3 (0.46 g, 3.32 mmol) following a procedure analogous to that described above for 10. Purification was carried out on a silica-gel column with the following eluents: First with 100% CH2Cl2 and then 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2. The product was isolated as pale yellow oil (65%). 1H NMR (CDCl3) δ 8.491 (m, 1H, Ar), 7.624 (m, 1H, Ar), 7.512 (t, 1H, Ar), 7.111 (m, 2H, Ar), 7.010 (m, 2H, Ar), 3.750 (s, 2H, —CH2—), 3.690 (s, 2H, —CH2—), 3.513 (ddd, 2H, —CH2—), 2.616 (t, 2H, —CH2—), 1.946 (m, 2H, —CH2—), 1.354 (s, 9H, —C(CH3)3). Mass Spec.=346.89 (M+H)+.

후처리

  1. customPurification

출처 및 근거

ORD 기록
ord-1dd882d0a72d44769a0f2b4def352e38
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747810B2

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