Acetyl chloride → HCID 67751568, compound

HRID 2210690Notes

Reaction equation

HRID 2210690 reaction equation
C([Cl:4])(=O)C.[CH3:5][C:6]1[CH:7]=[C:8]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[C:10]([CH3:12])[CH:11]=1>CO>[ClH:4].[CH3:12][C:10]1[CH:9]=[C:8]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:6]([CH3:5])[CH:11]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67751569HCID 67751569, compound

Product 1

HCID 67751568HCID 67751568, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetyl chloride (0.26 ml, 3.66 mmol) was added dropwise with stirring to anhydrous methanol (3.7 ml) and the resultant solution was added to a solution of cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpiperidine (360 mg, 1.22 mmol) in anhydrous methanol (1 ml). The solvent was removed in vacuo, and the residue recrystallised from ethyl acetate-methanol to provide cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenyl piperidine hydrochloride salt as a crystalline, white solid, m.p.=200°-225° C. (decomp). 1H NMR (360 MHz, DMSO-d6) δ7.44 (m), 6.82 (2), 6.56 (2), 4.49 (2), 4.41 (d, J=12.3 Hz), 4.09 (d, J=12.3 Hz), 3.80 (s), 3.05 (t, J=14.7 Hz), 2.14 (s), 1.90 (m), 1.72 (m); m/z (CI+) 296 (MH); Analysis: Found: C, 72.36; H, 7.91; N, 4.31. Calcd. for C20H26NOCl; C, 72.38; H, 7.90; N, 4.22%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue recrystallised from ethyl acetate-methanol

Sources & evidence

ORD record
ord-c7922ee4cf304fc882ebbe012339c816
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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