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

HRID 2280934Notes

Reaction equation

HRID 2280934 reaction equation
C(N1CCC(NC)CC1)C1C=CC=CC=1.[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:42])[C:30](=[O:41])[CH2:31][O:32][C:33]2[N:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[N:34]=2)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[ClH:43].C(OCC)(=O)C>CO>[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:42])[C:30](=[O:41])[CH2:31][O:32][C:33]2[N:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[N:34]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[ClH:43].[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:42])[C:30](=[O:41])[CH2:31][O:32][C:33]2[N:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[N:34]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 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)oxyaceteic 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-f8bd59201f104ff887d6508e077b79a7
Source dataset
uspto-grants-2015_09
Patent number
US09139559B2

Reaction notes

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