Ammonia → HCID 86733841, compound

HRID 1283533Notes

Reaction equation

HRID 1283533 reaction equation
[NH2:1][CH2:2][C:3]1(N2CCCCC2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=O.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N.[OH2:32]>CCOCC>[Cl:15][CH:16]1[CH2:24][CH2:23][CH2:22][CH2:21][C:17]1([CH2:18][NH:1][C:2](=[O:32])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 962WaterHCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 3984021-[1-(Piperidin-1-yl)cyclohexyl]methanamine

Product 1

HCID 86733841HCID 86733841, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(1-aminomethylcyclohexyl) piperidine (1.5 g.), 2-chlorobenzoyl chloride (2 ml) and pyridine (10 ml) was allowed to stand at room temperature for 1 hr. with no apparent effect. The mixture was therefore refluxed for 1 hr., cooled, diluted with water, basified with ammonia and extracted with chloroform. This chloroform extract was washed with water, dried (Na2SO4), and evaporated to give a viscous, brown oil (3.0 g. 79.2%). On dissolving in ether and bubbling dry HCl gas into the solution pale buff rosettes of 1-(2-chlorobenzamidomethylcyclohexyl) piperidine hydrochloride, m.p. 234°-6° were obtained (from -ethanol/ether.

Workup

  1. temperatureThe mixture was therefore refluxed for 1 hr
  2. temperature, cooled
  3. extractionextracted with chloroform
  4. extractionThis chloroform extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a viscous, brown oil (3.0 g. 79.2%)
  9. custombubbling dry HCl gas into the solution pale buff rosettes of 1-(2-chlorobenzamidomethylcyclohexyl) piperidine hydrochloride
  10. customm.p. 234°-6° were obtained (from -ethanol/ether

Sources & evidence

ORD record
ord-6bae2a885fee48ec8fdbe44eea78f186
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

Loading…