Hydrochloric Acid → HCID 12898843, compound

HRID 1277860Notes

Reaction equation

HRID 1277860 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][CH:10]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl.[H][H]>[Pd].C(O)C>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][CH:10]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11]2)=[O:8])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12898865HCID 12898865, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12898843HCID 12898843, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 20 g. (0.067 mole) of 4-cyano-N-(1-cyclohexyl-3-pyrrolidinyl)benzamide in 400 ml. of 95% ethanol and 19.24 g. (0.202 mole) of concentrated hydrochloric acid containing 2.0 g. of palladium on charcoal (10%) was shaken at room temperature in three atmospheres of hydrogen for five hours. The filtered mixture was concentrated at reduced pressure and the residue was partitioned between dilute sodium hydroxide and chloroform. The dried chloroform solution was concentrated at reduced pressure and the residue was recrystallized from ethyl acetate to give 8.0 g. (40%) of product which melted at 125°-129° C.

Workup

  1. concentrationThe filtered mixture was concentrated at reduced pressure
  2. customthe residue was partitioned between dilute sodium hydroxide and chloroform
  3. concentrationThe dried chloroform solution was concentrated at reduced pressure
  4. customthe residue was recrystallized from ethyl acetate
  5. customto give 8.0 g

Sources & evidence

ORD record
ord-7ee474551fe740799f1ae3517da191fa
Source dataset
uspto-grants-1981_07
Patent number
US04279822

Reaction notes

Loading…