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

HRID 864380Notes

Reaction equation

HRID 864380 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7a6e59f5ab8345ad8252c45e7c6cfeed
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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