HCID 10489880, compound → HCID 10536915, compound

HRID 964004Notes

Reaction equation

HRID 964004 reaction equation
B.CSC.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([NH2:21])=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>O1CCCC1>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][NH2:21])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 10489880HCID 10489880, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10536915HCID 10536915, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulphide complex (15 ml; 10M in dimethyl sulphide) was added dropwise at 15°-20° C., under nitrogen, to a stirred suspension of 1-(4-methoxyphenyl) piperidine-4-carboxamide (10 g) in tetrahydrofuran (95 ml). The mixture was heated under reflux for 4 hours then allowed to stand at ambient temperature for 16 hours. Ice water was added to destroy excess reducing agent then the mixture was acidified by the addition of hydrochloric acid (5M) and washed with ether (200 ml). The aqueous layer was basified by the addition of concentrated aqueous sodium hydroxide solution then the product was extracted into ether (3×250 ml). The combined extracts were dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified by flash chromatography over silica using a 9:1 mixture of dichloromethane and industrial methylated spirit as eluant. The solvents were removed in vacuo from the appropriate fractions to give 1-[1-(4-methoxyphenyl)-piperid-4-yl]methylamine as an oil (0.5 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customto destroy excess
  4. additionthe mixture was acidified by the addition of hydrochloric acid (5M)
  5. washwashed with ether (200 ml)
  6. additionThe aqueous layer was basified by the addition of concentrated aqueous sodium hydroxide solution
  7. extractionthe product was extracted into ether (3×250 ml)
  8. dry with materialThe combined extracts were dried over magnesium sulphate
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by flash chromatography over silica using
  11. additiona 9:1 mixture of dichloromethane and industrial methylated spirit as eluant
  12. customThe solvents were removed in vacuo from the appropriate fractions

Sources & evidence

ORD record
ord-a8ab73ca845e448cb943f01fe30602ea
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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