Propionyl chloride → 1-Phenyl-1'-propionylspiro[indoline-3,4'-piperidine]

HRID 1702016Notes

Reaction equation

HRID 1702016 reaction equation
[C:1]1([N:7]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9]3([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](Cl)(=[O:24])[CH2:22][CH3:23].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]1([N:7]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9]3([CH2:10][CH2:11][N:12]([C:21](=[O:24])[CH2:22][CH3:23])[CH2:13][CH2:14]3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 20442643HCID 20442643, compound

Product 1

HCID 204426541-Phenyl-1'-propionylspiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-phenylspiro[indoline-3,4'-piperidine] (Example 11), propionyl chloride and sodium bicarbonate in chloroform is stirred at reflux. The mixture is permitted to cool, filtered, and the filtrate concentrated, leaving 1-phenyl-1'-propionylspiro[indoline-3,4'-piperidine]. In a similar fashion, 1-phenylspiro[indoline-3,4'-piperidine] is treated with benzoylchloride to provide 1'-benzoyl-1-phenylspiro[indoline-3,4'-piperidine].

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-13e75812670245f88e79035b914bc9a7
Source dataset
uspto-grants-1983_04
Patent number
US04379932

Reaction notes

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