Sodium Cyanide → HCID 18768971, 화합물

HRID 480245노트

반응식

HRID 480245 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 18768971HCID 18768971, 화합물

시약·촉매·용매 3

HCID 222Ammonia용매2회HCID 887Methanol용매3회HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-65f85fecaede4f73893a2cbed3358dad
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649642B2

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