4-Phenylpiperidin-4-ol → HCID 17877142, compound

HRID 1738933Notes

Reaction equation

HRID 1738933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:13]2[N:14]([CH3:24])[C:15](=[O:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:13]2[N:14]([CH3:24])[C:15](=[O:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:11][N:29]2[CH2:30][CH2:31][C:26]([OH:25])([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:27][CH2:28]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 21839789HCID 21839789, compound

Product 1

HCID 17877142HCID 17877142, compound

Procedure

3-[1-(3,4-Dichlorophenyl)-3-oxopropyl]-2-methyl-2H-isoquinolin-1-one (0.303 g) was coupled to 4-hydroxy-4-phenyl-piperidine (0.15 g) by method similar to that described in Example 1. After aqueous work up, the product was purified by column chromatography. Eluting with ethyl acetate, followed by dichloromethane:methanol, (9:1) afforded the title compound as a solid; mp 100-102° C.; MS: m/z=521(M+1); NMR: 1.55 (t,2, J=12), 1.89 (m,2), 2.10 (m,1), 2.28 (m,5), 3.35 (s,3), 4.46 (broad,1), 6.90 (s,1), 7.17-7.71 (m,11), 8.18 (d,1, J=8). Analysis for C30H30Cl2N2O2.0.5 H2O: Calculated: C, 67.92; H, 5.89; N, 5.28; Found: C, 68.22; H, 5.86; N, 5.16.

Workup

  1. customAfter aqueous work up, the product was purified by column chromatography
  2. washEluting with ethyl acetate

Sources & evidence

ORD record
ord-23348629e2454e65826b6eaa3a5595c9
Source dataset
uspto-grants-1999_10
Patent number
US05965576

Reaction notes

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