Hydrochloric Acid → 1-[1-(4-Chlorophenyl)cyclobutyl]-2-methoxyethylamine hydrochloride

HRID 728293Notes

Reaction equation

HRID 728293 reaction equation
C([BH3-])#[N:2].[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:16](=O)[CH2:17][O:18][CH3:19])[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C([O-])(=O)C.[NH4+].C(=O)([O-])[O-].[Na+].[Na+].S(=O)(=O)(O)O.Cl>CC(O)C.O.CO>[ClH:5].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH:16]([NH2:2])[CH2:17][O:18][CH3:19])[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 198236811-[1-(4-Chlorophenyl)cyclobutyl]-2-methoxyethanone

Product 1

HCID 679455781-[1-(4-Chlorophenyl)cyclobutyl]-2-methoxyethylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Sodium cyanoborohydride (4 g) was added to a stirred mixture of 1-[1-(4-chlorophenyl)cyclobutyl]-2methoxyethanone (20 g), ammonium acetate (70 g) and methanol (300 ml) and the mixture allowed to stand at ambient temperature for 10 days. The mixture was poured into water (1 litre), basified with aqueous sodium carbonate solution and extracted with ether. The extract was evaporated to yield an oil which was poured into water, acidified with concentrated sulphuric acid and allowed to stand for 16 hours at ambient temperature and then heated to 90°-95° C. for 1 hour. The cooled mixture was washed with ether, basified and extracted with ether. The extracts were dried and evaporated to give an oil which was treated with concentrated hydrochloric acid and propan-2-ol. Evaporation to dryness gave a solid which was recrystallised from propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethylamine hydrochloride (m.p. 207°-210° C.).

Workup

  1. extractionextracted with ether
  2. customThe extract was evaporated
  3. customto yield an oil which
  4. waitto stand for 16 hours at ambient temperature
  5. temperatureheated to 90°-95° C. for 1 hour
  6. washThe cooled mixture was washed with ether
  7. extractionextracted with ether
  8. customThe extracts were dried
  9. customevaporated
  10. customto give an oil which
  11. customEvaporation to dryness
  12. customgave a solid which
  13. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-be8e9df13e3441fa820db6a24e69dea5
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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