Methyl p-toluenesulfonate → HCID 86734278, compound

HRID 1973687Notes

Reaction equation

HRID 1973687 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(OCC)(=O)C>[C:26]1([CH3:29])[CH:25]=[CH:24][C:23]([S:20]([O-:22])(=[O:19])=[O:21])=[CH:28][CH:27]=1.[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N+:13]2([CH3:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 191031HCID 191031, compound

Product 1

HCID 86734278HCID 86734278, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

cis- 2Phenyl-1-pyrrolidinocyclohexane (2.3g) and methyl-p-toluenesulphonate (1.9g) were heated in boiling ethyl acetate under reflux for 18 hours. An oil slowly formed which quickly crystallised on cooling. Recrystallisation from ethyl alcohol/ethyl acetate afforded the quaternary salt (3.0g), m.p. 146° to 148° C

Workup

  1. temperatureunder reflux for 18 hours
  2. customAn oil slowly formed which
  3. customquickly crystallised
  4. temperatureon cooling
  5. customRecrystallisation from ethyl alcohol/ethyl acetate

Sources & evidence

ORD record
ord-c8d6554cc4c34fe48b744e3498138091
Source dataset
uspto-grants-1976_12
Patent number
US03998843

Reaction notes

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