Triethylamine → HCID 22909583, compound

HRID 1379060Notes

Reaction equation

HRID 1379060 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:38][C:39](Cl)=[O:40])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]>C(Cl)Cl>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:38][C:39]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]2[CH2:8][CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:40])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 4544491HCID 4544491, compound

Product 1

HCID 22909583HCID 22909583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.65 g (0.01M) of 2-(2,2-diphenylethyl)piperidine in 25 ml of methylene chloride containing 1.5 ml of triethylamine was cooled in ice and a solution of 2.35 g (0.011M) of 3,4-di-methoxyphenylacetyl chloride in 25 ml of methylene chloride was added dropwise. The cooling bath was removed and the mixture was stirred at room temperature overnight. The mixture was then washed with dilute hydrochloric acid, water, dilute sodium hydroxide and saturated sodium chloride solution. Removal of the solvent left an oil which was purified by chromatography on silica gel. The solid thus obtained melted at 113°-114° C. after recrystallization from cyclohexane-ethyl acetate.

Workup

  1. customThe cooling bath was removed
  2. washThe mixture was then washed with dilute hydrochloric acid, water, dilute sodium hydroxide and saturated sodium chloride solution
  3. customRemoval of the solvent
  4. waitleft an oil which
  5. customwas purified by chromatography on silica gel
  6. customThe solid thus obtained melted at 113°-114° C. after recrystallization from cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-857268e8d3c74371b1560fecf6b4f08d
Source dataset
uspto-grants-1997_09
Patent number
US05670521

Reaction notes

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