Sodium Cyanide → HCID 18768971、化合物

HRID 427403ノート

反応式

HRID 427403 の反応式
[CH2:1]([N:8]([CH3:20])[CH2:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:21]#[N:22].[Na+].[NH4+:24].[Cl-]>N.CO.C(Cl)Cl>[NH2:24][C:10]([CH2:9][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:20])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]#[N:22]

参加物

7

反応物 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 187689821-(Benzyl-methyl-amino)-4-phenyl-butan-2-one

生成物 1

HCID 18768971HCID 18768971、化合物

試薬・触媒・溶媒 3

HCID 222Ammonia溶媒2 回HCID 887Methanol溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

1-(Benzyl-methyl-amino)-4-phenyl-butan-2-one (2.4 g, 9.0 mmol, 1.0 equiv) was mixed in 36 mL of 2.0 M NH3 in MeOH. To the solution was added NaCN (0.484 g, 9.9 mmol, 1.1 equiv) and NH4Cl (0.528 g, 9.9 mmol, 1.1 equiv). The resulting mixture was refluxed for 2 h at which time an addition 15 mL of 2.0 M NH3 in MeOH was added and the mixture was refluxed another 4 h. Though TLC (5% MeOH in CH2Cl2) still showed the presence of the ketone, the reaction was cooled and filtered. The filtrate was concentrated and the crude product was purified by flash chromatography on SiO2 using 60% hexanes in CH2Cl2 then 1.5% MeOH to 3% MeOH was added. The desired product was isolated pure (0.561 g, 21%) as a yellow oil that crystallized upon standing at −20° C.; MS, m/z 294=M+1.

後処理

  1. temperatureThe resulting mixture was refluxed for 2 h at which time
  2. additionwas added
  3. temperaturethe mixture was refluxed another 4 h
  4. temperaturethe reaction was cooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by flash chromatography on SiO2 using 60% hexanes in CH2Cl2
  8. addition1.5% MeOH to 3% MeOH was added

出典と根拠

ORDレコード
ord-a8c9c154250a4b38976d5a91d0138133
出典データセット
uspto-grants-2001_11
特許番号
US06313117B1

反応ノート

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