3-Pyridinebutanoic acid → 4-Diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine

HRID 1249568Notes

Reaction equation

HRID 1249568 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])[CH:21]=1>CN(C)C=O.C(N(CC)CC)C.ClCCl>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([C:29](=[O:30])[CH2:28][CH2:27][CH2:26][C:22]3[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 1143-Pyridinebutanoic acidHCID 882784-Benzhydrylpiperidine

Product 1

HCID 202234374-Diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidineYield 88.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2.0 g of 4-diphenylmethylpiperidine in 5 mL of dimethylformamide and 4.2 mL of triethylamine was treated at 0° C. with a solution composed of 5 mL of dimethylformamide and the acid chloride prepared from 2.0 g of 3-pyridine butanoic acid. After 15 minutes the mixture was diluted with dichloromethane, filtered and evaporated to dryness. The residue was partitioned between toluene and 1N sodium hydroxide and the organic layer was washed with brine, dried over sodium sulfate and evaporated to give 3.3 g of crude oil. Purification was accomplished by chromatography on a Waters Prep 500 HPLC using silica gel columns and eluting with 98:2 ethyl acetate-triethylamine. The product consisted of a colorless oil which was dried under vacuum at 70° C. to give 2.8 g (86%) of 4-diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine, 0.1 molar ethylacetate solvate. Analysis Calculated for C27H30N2O.O.1C4H8O 2 : C, 80.79; H, 7.62; N, 6.88. Found: C, 80.91; H, 7.57; N, 6.81.

Workup

  1. additionwas treated at 0° C. with a solution
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue was partitioned between toluene and 1N sodium hydroxide
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give 3.3 g of crude oil
  9. customPurification
  10. washeluting with 98:2 ethyl acetate-triethylamine
  11. customwas dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-c3625b755fe545eaaa09b02d8d1f106a
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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