Ammonia → HCID 68124883, compound

HRID 436665Notes

Reaction equation

HRID 436665 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)#[N:2].N.NCCCCCCCN[C:33](=[O:45])[C:34]1[CH:39]=[CH:38][C:37](OC(F)(F)F)=[CH:36][CH:35]=1.Cl.[CH2:47]([OH:49])C>[Ni]>[CH3:47][O:49][CH:5]([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:22])[C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:15][CH:16]=1)[CH2:4][CH2:3][CH2:1][NH:2][C:33](=[O:45])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 20308195HCID 20308195, compoundHCID 20308196N-(6-Cyanohexyl)-4-(trifluoromethoxy)benzamide

Product 1

HCID 68124883HCID 68124883, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture containing 12 g. of N-(6-cyanohexyl)-4-trifluoromethoxybenzamide in 100 ml. of ethanol, 8 g. of ammonia and 4 g. of Raney nickel was hydrogenated at approximately 30° C. for a period of 5 hours. The reaction mixture was filtered and the solvent and excess ammonia were removed by heating in vacuo. The residual material was dissolved in 150 ml. of isopropyl alcohol acidified with ethanolic hydrogen chloride and the solution was concentrated in vacuo to about 100 ml. The solution was cooled in an ice bath and the solid that separated was collected, washed with cold isopropyl alcohol and ether, and dried at 60° C. in vacuo to yield 9 g. of N-(7-aminoheptyl)-4-trifluoromethoxybenzamide as its hydrochloride, m.p. 178°-181° C.

Workup

  1. additionA mixture containing 12 g
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent and excess ammonia were removed
  4. temperatureby heating in vacuo
  5. dissolutionThe residual material was dissolved in 150 ml
  6. concentrationthe solution was concentrated in vacuo to about 100 ml
  7. temperatureThe solution was cooled in an ice bath
  8. customthe solid that separated
  9. customwas collected
  10. washwashed with cold isopropyl alcohol and ether
  11. customdried at 60° C. in vacuo
  12. customto yield 9 g

Sources & evidence

ORD record
ord-09b8cfa10e944a16a20dd737f0b5ca38
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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