Hydrochloric Acid → HCID 13083334, compound

HRID 325873Notes

Reaction equation

HRID 325873 reaction equation
C([NH:3][CH:4]([CH3:17])[CH2:5][C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7]1)=O.Cl.O>CCOCC>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([C:6]2([CH2:5][CH:4]([NH2:3])[CH3:17])[CH2:9][CH2:8][CH2:7]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13083337HCID 13083337, compound

Product 1

HCID 13083334HCID 13083334, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-formyl-2-[1-(4-chlorophenyl)cyclobutyl]-1-methylethylamine (11.06 g) prepared as described above was heated under reflux for six hours with a mixture of concentrated hydrochloric acid (34 ml), water (34 ml) and diethyleneglycoldimethyl ether (40 ml). The mixture was cooled, washed with ether and basified with aqueous sodium hydroxide. The basified solution was extracted into ether, washed with water, dried, evaporated and distilled to give 2-[1-(4-chlorophenyl)cyclobutyl]-1-methylethylamine (b.p. 119°-121° C. at 0.8 mm Hg). The amine (2.65 g) was dissolved in propan-2-ol (15 ml) and concentrated hydrochloric acid added to pH 2. Ether (110 ml) was added and crystals of 2-[1-(4-chlorophenyl) cyclobutyl]-1-methylethylamine hydrochloride (m.p. 184°-185° C.) were collected. (Formula I R1, R2 =H; R3, R4 =H; R5 =4-Cl; R6 =H; R7 =Me and R8 =H.)

Workup

  1. temperatureabove was heated
  2. temperatureThe mixture was cooled
  3. washwashed with ether and basified with aqueous sodium hydroxide
  4. extractionThe basified solution was extracted into ether
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. distillationdistilled

Sources & evidence

ORD record
ord-9ec1aea9089348b5886abb919814a6d5
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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