Ammonia → HCID 67543426, compound

HRID 2355828Notes

Reaction equation

HRID 2355828 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH2:23][C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=O)[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].N>CO.C(Cl)Cl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:15]([C@H:24]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)[CH2:23][N:19]4[CH2:20][CH2:21][CH2:22][C@H:18]43)=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67543507HCID 67543507, compound

Product 1

HCID 67543426HCID 67543426, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-{2-[3-(1-Isopropyl-piperidin-4-ylmethoxy)-phenyl]-pyrrolidin-1-yl}-(4-methoxy-phenyl)-ethanone. Prepared as described in Example 8, Step 1, on a 3.31 mmol scale, to give 1.04 g (70%) of the desired product as a pale yellow oil after chromatography (NH3 in MeOH/CH2Cl2). MS: exact mass calcd for C27H36N2O3, 450.3; m/z found, 451.5 [M+H]+. 1H NMR (MeOH-d4): 7.84 (m, 2H), 7.20 (m, 1H), 7.01 (d, J=1.5, 1H), 6.96 (d, J=7.5, 1H), 6.92 (m, 2H), 6.81 (m, 1H), 4.89 (s, 1H), 3.96 (d, J=16.6, 1H), 3.86 (m, 5H), 3.46 (m, 3H), 3.29 (m, 3H), 2.80 (t, J=12.3, 2H), 2.33 (m, 1H), 2.18 (m, 1H), 2.02 (m, 4H), 1.87 (m, 1H), 1.75 (m, 1H), 1.64 (m, 2H), 1.28 (d, J=6.7, 6H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-df90c7db994d47f9a830436a28938e02
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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