Hydrochloric Acid → N-[(5-chloro-6-methyl-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride

HRID 420735Notes

Reaction equation

HRID 420735 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:5]=[N:6][C:7]=1[CH3:8].[ClH:24]>C(Cl)Cl>[ClH:1].[ClH:24].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH:5]=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580017711,1-Dimethylethyl 4-{[(5-chloro-6-methyl-3-pyridinyl)methyl]amino}-1-piperidinecarboxylate

Product 1

HCID 66658600N-[(5-chloro-6-methyl-3-pyridinyl)methyl]-4-piperidinamine dihydrochlorideYield 206.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{[(5-chloro-6-methyl-3-pyridinyl)methyl]amino}-1-piperidinecarboxylate (65.58 g, 193 mmol) in DCM (800 ml) at 0° C. was treated with HCl (4M solution in 1,4-dioxane, 386 ml, 1544 mmol) and stirred at room temperature overnight. The resulting white suspension was filtered, washed with DCM and hexane and dried to obtain N-[(5-chloro-6-methyl-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (62.3 g) as a white solid. The crude product was dissolved in DCM/MeOH 5% (800 ml) and 2N NaOH (500 ml) was added until pH 13.8. Organic phase was extracted and aqueous phase was extracted again with DCM/MeOH 10% (650 ml×2). Combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated under vacuum to give N-[(5-chloro-6-methyl-3-pyridinyl)methyl]-4-piperidinamine (44.82 g, 97%).

Workup

  1. filtrationThe resulting white suspension was filtered
  2. washwashed with DCM and hexane
  3. customdried

Sources & evidence

ORD record
ord-b80243e1085b4e41a2752b678ba75926
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

Loading…