N-(4-Phenylpiperidin-4-yl)acetamide → HCID 21839969, compound

HRID 1738974Notes

Reaction equation

HRID 1738974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:25]([NH:28][C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:27])[CH3:26]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH2:11][N:32]2[CH2:31][CH2:30][C:29]([NH:28][C:25](=[O:27])[CH3:26])([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:34][CH2:33]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 21839905HCID 21839905, compound

Product 1

HCID 21839969HCID 21839969, compoundYield 101.5%

Procedure

3-(3,4-Dichlorophenyl)-3-(6-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (1.5 g) was coupled to 4-acetamido-4-phenylpiperidine (0.7 g) by a method similar to that described in Example 8. The reaction product was purified by chromatography and converted to the corresponding hydrochloride salt as described in Example 8 to afford the title compound (1.26 g); mp 212-225° C.; MS: m/z=566(m+1); NMR: 2.00 (s,3), 2.22(m,5), 2.5 (m,2), 2.7(m,2), 2.99(s,3), 3.54(m,1), 4.54 (d,1, J=3.4), 5.81 (s,1), 6.6 (m,1), 6.7 (m,1), 6.97 (m,1), 7.11 (m,2), 7.31 (m,6), 7.50 (d,1, J=8).

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-de24f747e0734136977ec00dfbb0c087
Source dataset
uspto-grants-1999_10
Patent number
US05965576

Reaction notes

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