1-benzyl-N-methylpiperidin-4-amine → N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamide

HRID 1749304Notes

Reaction equation

HRID 1749304 reaction equation
CC1C=C(C)N=C(OCC(O)=O)N=1.C(N1CCC(NC)CC1)C1C=CC=CC=1.[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:55])[C:43](=[O:54])[CH2:44][O:45][C:46]2[N:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[N:47]=2)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[ClH:56].C(OCC)(=O)C>CO>[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:55])[C:43](=[O:54])[CH2:44][O:45][C:46]2[N:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[N:47]=2)[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1.[ClH:56].[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:55])[C:43](=[O:54])[CH2:44][O:45][C:46]2[N:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[N:47]=2)[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 198818052-((4,6-Dimethylpyrimidin-2-yl)oxy)acetic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 59336186N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamide

Product 2

HCID 59336186N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamideYield 62%HCID 68416141N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamide (147 mg: 62% yield) was synthesized from 2-(4,6-dimethylpyrimidine-2-yl)oxyacetic acid (117 mg) and 1-benzyl-N-methylpiperidine-4-amine (131 mg) in the same manner as in Example 49. Then, to a methanol solution of N-(1-benzylpiperidine-4-yl)-2-(4,6-dimethylpyrimidine-2-yloxy)-N-methylacetamide, 1 equivalent of 4N HCl/ethyl acetate solution was added. The mixture was then concentrated under reduced pressure to give the desired product as a white amorphous.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-958769acabf84a1b8029a01fb893427a
Source dataset
uspto-grants-2015_10
Patent number
US09156817B2

Reaction notes

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