Hydrochloric Acid → HCID 9849961, compound

HRID 2256020Notes

Reaction equation

HRID 2256020 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:28][CH:27]=[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CO.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:27][CH2:28]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19029107HCID 19029107, compound

Product 1

HCID 9849961HCID 9849961, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of N-[2-(3,4-dichlorophenyl)-4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-N-methylbenzamide (0.28 g) in methanol (10 mL) was treated with methanolic hydrogen chloride (2 mL), and 10% (w/w) palladium on carbon (0.03 g) was added. The reaction mixture was subjected to hydrogenation at atmospheric pressure for 2.5 hours. At the end of this period, the reaction mixture was treated with additional 10% palladium on carbon (0.03 g); and the hydrogenation was continued for an additional 16 hours. The reaction mixture was filtered through diatomaceous earth and evaporated. The resulting material was treated with ether and evaporated; and the process was repeated twice. The residue was crystallized from a mixture of ethyl acetate, methanol, ether and hexane; washed with a mixture of ether and hexane; and dried under vacuum to afford the title compound as a white solid (0.11 g); mp 142°-148° C.; NMR (CD3OD): 1.8-2.4 (m, 6), 2.6-3.2 (m, 9), 3.5-3.9 (m, 4), 7.0-7.6 (m, 13); MS: m/z=495(M+1). Analysis for C29H32Cl2N2O·HCl·H2O: Calculated: C, 63.33; H, 6.41; N, 5.09; Found: C, 63.46; H, 6.12; N, 5.13.

Workup

  1. additionwas added
  2. waitand the hydrogenation was continued for an additional 16 hours
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. customevaporated
  5. additionThe resulting material was treated with ether
  6. customevaporated
  7. customThe residue was crystallized from a mixture of ethyl acetate, methanol, ether and hexane
  8. washwashed with a mixture of ether and hexane
  9. customand dried under vacuum

Sources & evidence

ORD record
ord-f26c1f1f394f4bc987940343f6b81611
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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