Benzyl Bromide → Tert-butyl 3-(benzylamino)benzylcarbamate

HRID 2071005노트

반응식

HRID 2071005 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>CN(C=O)C.O>[CH2:17]([NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

생성물 1

HCID 68670447Tert-butyl 3-(benzylamino)benzylcarbamate수율 30.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of the starting tert-butyl 3-aminobenzylcarbamate (0.925 g, 4.16 mmol, 1 eq, derived from 3-(aminomethyl)aniline (TCI America)) in 10 ml anhydrous DMF under Ar was treated with benzyl bromide (0.54 ml, 0.78 g, 4.58 mmol, 1.1 eq) and Et3N (0.75 ml, 0.55 g, 1.3 eq). After stirring for 48 h the reaction was diluted with water and extracted with EtOAc (×2). The combined organics were washed with water (×4), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3937 g (1.26 mmol, 30% yield) of tert-butyl 3-(benzylamino)benzylcarbamate.

후처리

  1. extractionextracted with EtOAc (×2)
  2. washThe combined organics were washed with water (×4), brine (×1)
  3. dry with materialdried over Na2SO4
  4. filtrationThe inorganics were filtered off
  5. customthe solvent was removed in vacuo
  6. customPurification via flash chromatography

출처 및 근거

ORD 기록
ord-5cae4fff012945eca2a35149b4a204f9
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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