Methylamine → 2-(Methylamino)-2-oxoethyl 2-[1-(6-isobutyl-2-pyridyl)-4-piperidyl]ethylcarbamate

HRID 1663053Notes

Reaction equation

HRID 1663053 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][N:19]3[C:23](=[O:24])[CH2:22][O:21][C:20]3=[O:25])[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:26][NH2:27]>O1CCCC1>[CH2:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][NH:19][C:20](=[O:25])[O:21][CH2:22][C:23]([NH:27][CH3:26])=[O:24])[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 210969683-{2-[1-(6-Isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione

Product 1

HCID 588612582-(Methylamino)-2-oxoethyl 2-[1-(6-isobutyl-2-pyridyl)-4-piperidyl]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The process is performed according to the procedure described in Example 1 (step 1.5). Starting with 0.72 g (2.08 mmol) of 3-{2-[1-(6-isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione, obtained in step 13.4, and 5.20 ml (10.40 mmol) of a solution (2M) of methylamine in tetrahydrofuran, and after chromatography on silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, followed by crystallization from diisopropyl ether, 0.540 g of pure product is obtained in the form of a white solid.

Sources & evidence

ORD record
ord-071f92228e78403cb0ba03935c85625c
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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