Hydrochloric Acid → HCID 13083333, compound

HRID 325870Notes

Reaction equation

HRID 325870 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:13](=O)[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:16][NH:17]C=O.CN.Cl>O.C(O)=O>[ClH:1].[CH3:16][NH:17][CH:13]([CH3:14])[CH2:12][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 31254N-MethylformamideHCID 13083375HCID 13083375, compound

Product 1

HCID 13083333HCID 13083333, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

The ketone prepared as described above (5.4 g) was mixed with N-methylformamide (18 ml), 98% formic acid (4 ml) and 25% aqueous methylamine (0.6 ml) and the mixture heated under reflux for sixteen hours. The mixture was poured into water and extracted with dichloromethane. The extract was washed, dried and evaporated to give a residue which was heated under reflux with concentrated hydrochloric acid (10 ml) for six hours. The mixture was evaporated to dryness and the residue dried by repeated addition and vacuum evaporation of an industrial methylated spirit/toluene mixture. The solid residue was recrystallised from propan-2-ol to give N-methyl-2-[1-(4-chlorophenyl)-cyclobutyl]-1-methylethylamine hydrochloride (m.p. 193°-194° C.) (Formula I R1, R2 =H; R3 =Me; R4 =H; R5 =4-Cl; R6 =H; R7 =Me; R8 =H).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for sixteen hours
  3. extractionextracted with dichloromethane
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customto give a residue which
  8. temperaturewas heated
  9. customThe mixture was evaporated to dryness
  10. customthe residue dried
  11. additionaddition and vacuum evaporation of an industrial methylated spirit/toluene mixture
  12. customThe solid residue was recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-ae02d2371276454b8649b69bf49622e1
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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