Hydrochloric Acid → HCID 19823714, compound

HRID 1650950Notes

Reaction equation

HRID 1650950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])C(=O)C)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH3:20].C(Br)C.[Mg].Cl.CC[O:30][CH2:31][CH3:32]>CC(C)=O.CC(O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])[C:31]([CH3:32])([OH:30])[CH2:19][CH3:20])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric Acid2×HCID 3283Diethyl Ether3×HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 19823745HCID 19823745, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 19823714HCID 19823714, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one (10 g prepared as described in Example 47) in dry ether (25 ml) was added dropwise to a stirred solution of ethyl magnesium bromide prepared by the reaction of a solution of ethyl bromide (5 ml) in dry ether (20 ml) with magnesium (1.3 g) in dry ether (160 ml). The mixture was stirred for two hours at ambient temperature and water (60 ml) and then 5N hydrochloric acid (60 ml) were added. The mixture was allowed to stand for 16 hours and the aqueous layer was separated, washed with ether, basified and extracted with ether. The extract was dried and the ether removed to give an oil which was treated with a mixture of excess concentrated hydrochloric acid and propan-2-ol. Evaporation yielded a gum which was dissolved in acetone. The volume of the acetone solution was reduced and a solid precipitated which was collected and recrystallised from propan-2-ol to give 1-[1 -(4-chlorophenyl)cyclobutyl]-1-dimethylamino-2-methylbutan-2-ol hydrochloride (m.p. 167°-170° C. (dec)).

Workup

  1. waitto stand for 16 hours
  2. customthe aqueous layer was separated
  3. washwashed with ether
  4. extractionextracted with ether
  5. customThe extract was dried
  6. customthe ether removed
  7. customto give an oil which
  8. customEvaporation
  9. customyielded a gum which
  10. customa solid precipitated which
  11. customwas collected
  12. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-390e5e77072e42aa8661f76b438c7089
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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