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

HRID 2071005ノート

反応式

HRID 2071005 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 68670447Tert-butyl 3-(benzylamino)benzylcarbamate収率 30.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5cae4fff012945eca2a35149b4a204f9
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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