Hydrochloric Acid → 1-(2-Chloropyridin-4-yl)piperidin-4-amine dihydrochloride

HRID 451498Notes

Reaction equation

HRID 451498 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[ClH:22]>ClCCl>[ClH:1].[ClH:22].[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86656708tert-Butyl 1-(2-chloropyridin-4-yl)piperidin-4-ylcarbamate

Product 1

HCID 866567091-(2-Chloropyridin-4-yl)piperidin-4-amine dihydrochlorideYield 199.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(2-chloropyridin-4-yl)piperidin-4-ylcarbamate (1.00 g, 3.21 mmol) in dichloromethane (16 mL) was added HCl (2 M in diethylether, 8.02 mL, 16.0 mmol) and the reaction mixture was stirred at room temperature over night for 18 hours. The mixture was then filtered off and the white precipitate washed with dichloromethane and diethylether and dried to afford the title compound (913 mg, 99%) as a white solid. MS ISP (m/e): 212.1/214.1 [(M+H)+].

Workup

  1. filtrationThe mixture was then filtered off
  2. washthe white precipitate washed with dichloromethane and diethylether
  3. customdried

Sources & evidence

ORD record
ord-0ee34b7580454f07942e541b9b7384c2
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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