Water → 1'-Methyl-1-phenylspiro[indoline-3,4'-piperidine]

HRID 1702013Notes

Reaction equation

HRID 1702013 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:4][CH2:3]1.[H-].[Na+].F[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:8]2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 10008FluorobenzeneHCID 24758Sodium hydrideHCID 128015871'-Methylspiro[indoline-3,4'-piperidine]

Product 1

HCID 128015931'-Methyl-1-phenylspiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2.1 g of 1'-methylspiro[indoline-3,4'-piperidine] (Example 1b), 3 g of 50% sodium hydride and 12 ml of fluorobenzene in 18 ml of dimethyl sulfoxide is stirred at 65°-70° C. for 45 hours. The well stirred mixture is poured into water and extracted thrice with ether. The combined ether extracts are dried briefly before forming, the hydrochloride salt. The salt is collected, basified and then extracted into ether, giving a yellowish oil which is crystallized from hexane, producing off-white crystals, mp 90°-92° C. of 1'-methyl-1-phenylspiro[indoline-3,4'-piperidine].

Workup

  1. stirringThe well stirred mixture
  2. extractionextracted thrice with ether
  3. dry with materialThe combined ether extracts are dried briefly
  4. custombefore forming
  5. customThe salt is collected
  6. extractionextracted into ether
  7. customgiving a yellowish oil which
  8. customis crystallized from hexane

Sources & evidence

ORD record
ord-1761b2f4b6594457930a3841dfbfdacb
Source dataset
uspto-grants-1983_04
Patent number
US04379932

Reaction notes

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