Benzoyl chloride → HCID 70561340, compound

HRID 1413095Notes

Reaction equation

HRID 1413095 reaction equation
[CH3:1][N:2]1[CH2:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][C@H:4]([OH:14])[CH2:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:15]([O:14][C@H:4]1[CH2:5][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][N:2]([CH3:1])[CH2:3]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 70561140HCID 70561140, compound

Product 1

HCID 70561340HCID 70561340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cis-1-methyl-5-phenyl-3-piperidinol (3 g.) in dichloromethane (50 ml) was treated with benzoyl chloride (2.5 ml), the resulting mixture stirred for 2 hours at ambient temperature, and the solvent then removed under reduced pressure. The residue was partitioned between ether (100 ml) and 2 N HCl. The lower two of the three layers formed were basified to pH 9 with sodium carbonate and extracted with ether (2×100 ml). The organic phase was dried (over magnesium sulphate) and treated with excess ethereal HCl. The resulting oil crystallised on trituation with methanol/ethyl acetate to give the title compound as the hydrochloride hemi-hydrate (3.1 g;) m.p. 50°.

Workup

  1. customthe solvent then removed under reduced pressure
  2. customThe residue was partitioned between ether (100 ml) and 2 N HCl
  3. customThe lower two of the three layers formed
  4. extractionextracted with ether (2×100 ml)
  5. dry with materialThe organic phase was dried (over magnesium sulphate)
  6. additiontreated with excess ethereal HCl
  7. customThe resulting oil crystallised on trituation with methanol/ethyl acetate

Sources & evidence

ORD record
ord-e123eb33e3c44c53a7033520eff5bde7
Source dataset
uspto-grants-1981_02
Patent number
US04248876

Reaction notes

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