Sodium Cyanide → 4-Amino-4-cyano-1,2-dimethyl-piperidine

HRID 915225노트

반응식

HRID 915225 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH:3]1[CH3:9].[C-:10]#[N:11].[Na+].[NH4+:13].[Cl-]>N.CO>[NH2:13][C:5]1([C:10]#[N:11])[CH2:6][CH2:7][N:2]([CH3:1])[CH:3]([CH3:9])[CH2:4]1

참가 물질

6

반응물 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 124240391,2-Dimethylpiperidin-4-one

생성물 1

HCID 220631094-Amino-4-cyano-1,2-dimethyl-piperidine

시약·촉매·용매 2

HCID 222Ammonia용매2회HCID 887Methanol용매2회

실험 절차

1,2-Dimethyl-4-piperidone (1.23 g, 9.67 mmol, 1.0 equiv) was dissolved in 39 mL of 2 M NH3 in MeOH (8 equiv NH3). To this solution was added NaCN (0.52 g, 10.6 mmol, 1.1 equiv) and NH4Cl (0.57 g, 10.6 mmol, 1.1 equiv). The resulting mixture was refluxed for 2 h at which time an additional 39 mL of 2 M NH3 in MeOH was added followed by an additional 2 h of reflux. The reaction was cooled and filtered. The filtrate was concentrated and taken up in 100 mL of CH2Cl2 giving more salt precipitate which was removed by a second filtration. The filtrate was then concentrated to thick orange oil (1.32 g, 89%). 1H NMR showed a 3 to 1 mixture of diastereomers of unknown configuration. The crude product was used without further purification; MS, m/z 154=M+1.

후처리

  1. additionwas added
  2. temperatureof reflux
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customwas removed by a second filtration
  7. concentrationThe filtrate was then concentrated to thick orange oil (1.32 g, 89%)
  8. additionto 1 mixture of diastereomers of unknown configuration
  9. customThe crude product was used without further purification

출처 및 근거

ORD 기록
ord-c3988c24dfba4cb5a138e73c01c33e9e
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265132B2

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