Hydrochloric Acid → Tert-butyl 4-[3-(propylamino)pyridin-2-yl]piperazine-1-carboxylate

HRID 864380노트

반응식

HRID 864380 반응식
C([BH3-])#N.[Na+].[CH3:5][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[CH3:7].[CH3:25][CH2:26][CH:27]=O.Cl.[OH-].[NH4+]>ClCCl.CO>[CH3:7][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[C:22]([NH:23][CH2:25][CH2:26][CH3:27])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1)=[O:10])[CH3:5]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 527PropanalHCID 14923Ammonium HydroxideHCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 21477648Tert-butyl 4-[3-(propylamino)pyridin-2-yl]piperazine-1-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Sodium cyanoborohydride (0.31 g) is added to a cold solution of 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication No. WO 88/08424, 2.8 g), propional (0.87 g), and methanol (15 ml). After the exotherm has subsided, the reaction is stirred at 20°-25° overnight. The reaction is acidified (pH 2) with aqueous hydrochloride and then diluted with dichloromethane. The pH is adjusted with aqueous ammonium hydroxide (pH 8), and the phases are separated. The organic phase is dried over sodium sulfate, and concentrated under reduced pressure to a crude product which is dissolved in diethyl ether and allowed to crystallize at -5°. The solid is identified as starting material. The mother liquor is concentrated in vacuo to give the title compound.

후처리

  1. customthe phases are separated
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure to a crude product which
  4. dissolutionis dissolved in diethyl ether
  5. customto crystallize at -5°
  6. concentrationThe mother liquor is concentrated in vacuo

출처 및 근거

ORD 기록
ord-7a6e59f5ab8345ad8252c45e7c6cfeed
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563142

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