Hydrochloric Acid → 2-Amino-6-[(4-amino-1-piperidinyl)methyl]pyridine trihydrochloride salt

HRID 992738Notes

Reaction equation

HRID 992738 reaction equation
C(O)=O.CC(C)(C)C([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22]C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[N:10]=1)=O.[ClH:32]>CO>[ClH:32].[ClH:32].[ClH:32].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]2)[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 184131672-(Trimethylacetylamino)-6-[(4-t-butoxycarbonylamino-1-piperidinyl)methyl]pyridine formic acid salt

Product 1

HCID 701033962-Amino-6-[(4-amino-1-piperidinyl)methyl]pyridine trihydrochloride saltYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(trimethylacetylamino)-6-[(4-t-butoxycarbonylamino-1-piperidinyl)methyl]pyridine formic acid salt (0.74 g, 3.0 mmol) in methanol (6 mL) was added 6 N HCl (2 mL) at room temperature. The resulting mixture was heated to reflux for 10 h. Then, the reaction was cooled to room temperature and concentrated under rotary evaporator. After azeotropic removal of water with 1-propanol twice (20 mL each), the resulting solid was treated with methanol (5 mL). After being stirred for 1 h in methanol, ethanol (12 mL) was added slowly and stirred for additional 1 h. After filtration, drying of the resulting crystalline solid gave the desired title compound (491 mg, 80% yield, 98 A % purity).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 10 h
  3. concentrationconcentrated under rotary evaporator
  4. customAfter azeotropic removal of water with 1-propanol twice (20 mL each)
  5. additionthe resulting solid was treated with methanol (5 mL)
  6. additionethanol (12 mL) was added slowly
  7. stirringstirred for additional 1 h
  8. filtrationAfter filtration
  9. customdrying of the resulting crystalline solid

Sources & evidence

ORD record
ord-50368956fee247bfbc3d9eef2dbc50a4
Source dataset
uspto-grants-2002_10
Patent number
US06469172B2

Reaction notes

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