Ammonia → HCID 20351839, compound

HRID 435839Notes

Reaction equation

HRID 435839 reaction equation
[NH:1]([C:5]1[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][C:6]=1[CH2:7][N:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:9])C(C)=O.C(O)C.Cl.N>O>[NH2:1][C:5]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][C:6]=1[CH2:7][N:8]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH3:9]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 20351881HCID 20351881, compound

Product 1

HCID 20351839HCID 20351839, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21 gm of 2-acetamino-5-carbethoxy-N-cyclohexyl-N-methyl-benzylamine, 100 ml of ethanol, 90 ml of water and 60 ml of concentrated hydrochloric acid was refluxed for 1 hour. Thereafter, the reaction solution was cooled, poured over ice, made alkaline with ammonia and extracted three times with chloroform. The aqueous alkaline phase was evaporated to dryness in vacuo, the residue was thoroughly stirred with ethanol, and the mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was recrystallized from ethanol, yielding 2-amino-5-carboxy-N-cyclohexyl-N-methyl-benzylamine, m.p. 200°-205° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThereafter, the reaction solution was cooled
  3. additionpoured over ice
  4. extractionextracted three times with chloroform
  5. customThe aqueous alkaline phase was evaporated to dryness in vacuo
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated to dryness in vacuo
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-05380c9a8bcf40eabf8092985f2f975a
Source dataset
uspto-grants-1977_02
Patent number
US04006246

Reaction notes

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