Water → HCID 19823656, compound

HRID 1650981Notes

Reaction equation

HRID 1650981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=O)[CH2:13][S:14][CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:23].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH2:23])[CH2:13][S:14][CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 19823617HCID 19823617, compound

Product 1

HCID 19823656HCID 19823656, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 1-[1-(4-chlorophenyl)cyclobutyl]-2-methylthioethan-1-one (8.3 g prepared as described above), ammonium acetate (25 g) and sodium cyanoborohydride (2.6 g) were dissolved in methanol (120 ml). The solution was kept at room temperature for 19 days and then poured into water (300 ml) and basified to pH 8. The mixture was extracted with ether and the ethereal solution extracted with 2N hydrochloric acid. The acid solution was basified and extracted with ether. The extracts were dried and evaporated to give an oil which was purified by flash chromatography using ethyl acetate as eluant to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-methylthioethylamine the boiling point of which was not determined.

Workup

  1. extractionThe mixture was extracted with ether
  2. extractionthe ethereal solution extracted with 2N hydrochloric acid
  3. extractionextracted with ether
  4. customThe extracts were dried
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f1f2fbdc4f734897a27628dbaa5c4de1
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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