Hydrochloric Acid → HCID 178485424, compound

HRID 2209801Notes

Reaction equation

HRID 2209801 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.C=O.Cl.[CH2:27](Cl)[Cl:28]>[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:27][Cl:28])=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 178485423HCID 178485423, compound

Product 1

HCID 178485424HCID 178485424, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

33.8 g of trans-N-(4-chlorobenzoyl)-N-methyl-4-phenylcyclohexylamine, 24.3 g of paraformaldehyde and 24.3 g of zinc chloride are suspended in 1300 ml of methylene chloride at ambient temperature and over a period of 2.5 hours hydrogen chloride is introduced, whilst the temperature rises to 29° C. The solution obtained is stirred overnight, poured into 1500 ml of ice water and then stirred until phase separation is obtained. The organic phase is washed with water, dried and concentrated by evaporation and the residue is recrystallised from ethyl acetate. 30.1 g of the title compound, melting point 174°-176° C., are obtained.

Workup

  1. customrises to 29° C
  2. customThe solution obtained
  3. stirringstirred until phase separation
  4. customis obtained
  5. washThe organic phase is washed with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-8170b8cf24c140939ff3b26f2848e740
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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