Acetyl chloride → HCID 70624671, compound

HRID 2420095Notes

Reaction equation

HRID 2420095 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C@H:15]2[C@@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][NH:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]>C(Cl)Cl.[OH-].[Na+]>[C:1]([N:16]1[CH2:17][CH2:18][CH2:19][C@H:20]([OH:21])[C@@H:15]1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 70624201HCID 70624201, compound

Product 1

HCID 70624671HCID 70624671, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Acetyl chloride (9.75 g, 125 mmoles) is added dropwise to a cooled (0° to 10° C) and stirred solution of cis-2-(3,4-dimethoxyphenyl)-3-piperidinol (25.0 g, 105 mmoles, described in Example 4) in methylene chloride (200 ml) and 8N sodium hydroxide (100 ml). The mixture is stirred for 30 minutes and the organic phase is separated. The aqueous phase is extracted with methylene chloride. The organic extracts are washed with dilute hydrochloric acid, aqueous sodium carbonate, brine, dried (MgSO4) and evaporated. The residue is subjected to chromatography on silica gel using methanol-ether 1:3 and the eluates are evaporated to give cis-1-acetyl-2-(3,4-dimethoxyphenyl)-3-piperidinol; nmr (CDCl3) δ 2.12 (s, 3H), 3.86 (s, 6H) and 7.0 (m, 3H).

Workup

  1. temperaturea cooled (0° to 10° C)
  2. customthe organic phase is separated
  3. extractionThe aqueous phase is extracted with methylene chloride
  4. washThe organic extracts are washed with dilute hydrochloric acid, aqueous sodium carbonate, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customthe eluates are evaporated

Sources & evidence

ORD record
ord-572d786cca614118ab67358b7b1d17c3
Source dataset
uspto-grants-1978_08
Patent number
US04108997

Reaction notes

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