Cyclohexylamine → Glisindamide

HRID 894091Notes

Reaction equation

HRID 894091 reaction equation
C[O:2][C:3](=O)[NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:28])=[O:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH:30]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCOCC1>[O:28]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][N:19]1[C:17]([NH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([S:5]([NH:4][C:3]([NH:36][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:2])(=[O:6])=[O:7])=[CH:9][CH:10]=1)=[O:18]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 56634456HCID 56634456, compound

Product 1

HCID 3038458Glisindamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.2 g of N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-carbamic acid methyl ester (melting point 215°-217° C., prepared from 4-(2-[1-oxo-isoindoline-2-carboxamido]-ethyl)-benzenesulfonamide and methyl chloroformate) are dissolved in 100 ml of dioxane at 50° C. and 1 g of cyclohexylamine is added. The cyclohexylamine salt of the urethane, which precipitates, dissolves slowly on boiling under reflux for one hour. The mixture is concentrated to 1/3 of its volume and the residual solution is poured onto dilute hydrochloric acid. N-(4-[2-(1-Oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-urea, which is obtained in good yield, is filtered off and recrystallized from aqueous acetone. It melts at 214°-216° C.

Workup

  1. customThe cyclohexylamine salt of the urethane, which precipitates
  2. dissolutiondissolves slowly
  3. temperatureunder reflux for one hour
  4. concentrationThe mixture is concentrated to 1/3 of its volume
  5. additionthe residual solution is poured onto dilute hydrochloric acid

Sources & evidence

ORD record
ord-8f19bf987dc84232af2adbccf0748ef0
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

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