Benzoyl chloride → 1'-Benzoyl-1-phenylspiro[indoline-3,4'-piperidine]

HRID 67214Notes

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:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:21]([N:12]1[CH2:11][CH2:10][C:9]2([C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8]2)[CH2:14][CH2:13]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 20442643HCID 20442643, compound

Product 1

HCID 204426581'-Benzoyl-1-phenylspiro[indoline-3,4'-piperidine]

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].

Sources & evidence

ORD record: ord-3220a17cf51f4a21b4bcb22a212bd8e4
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04345081

Reaction notes

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