Water → HCID 23467208, compound

HRID 443428Notes

Reaction equation

HRID 443428 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][NH:11]2)[OH:9])=[CH:4][CH:3]=1.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]2([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]3[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[O:9]2)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 192201-Benzyl-4-piperidoneHCID 23467219HCID 23467219, compound

Product 1

HCID 23467208HCID 23467208, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 17 g alpha-(4-chlorophenyl)-2-piperidinemethanol, 15 g of N-benzyl-4-piperidone, and 0.3 g of p-toluenesulfonic acid in 150 ml of xylene is stirred under reflux for 48 hours in a vessel provided with a Dean-Stark water separator. The cooled mixture is filtered and evaporated in vacuo. The residue is crystallized from methanol to provide the product, hexahydro-1'-benzyl-1-(4-chlorophenyl)spiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine]; mp 134°-136° C.

Workup

  1. temperatureunder reflux for 48 hours in a vessel
  2. filtrationThe cooled mixture is filtered
  3. customevaporated in vacuo
  4. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-20fe4db57b0d47e281fc0939ca45c935
Source dataset
uspto-grants-1981_04
Patent number
US04260623

Reaction notes

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