Dimethylamine, hydrochloride → 1-BOC-4-DIMETHYLCARBAMOYLPIPERIDINE

HRID 1622320Notes

Reaction equation

HRID 1622320 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:19].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNC>C(Cl)(Cl)Cl.CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](=[O:13])[N:18]([CH3:19])[CH3:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 110215051-BOC-4-DIMETHYLCARBAMOYLPIPERIDINEYield 70.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

General procedure A was followed using N-Boc-isonipecotic acid (0.20 g, 0.86 mmol), HATU (0.43 g, 1.1 mmol), DIPEA (0.76 mL, 4.4 mmol), dimethylamine hydrochloride (92 mg, 1.1 mmol) and DMF (4 mL) to furnish the title compound as a pale brown oil (156 mg, 70%), umax (CHCl3)/cm−1 3020, 2861, 1684, 1631, 1417, 1367, 1151, 1030; m/z (ESI) C13H24N2NaO3 requires 279.1679, found [M+Na]+ 279.1677.

Sources & evidence

ORD record
ord-d2cfd42fcb4543bd8a6a644e5bfdd5d7
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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