Potassium Carbonate → HCID 14499769, compound

HRID 476633Notes

Reaction equation

HRID 476633 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[O:8])[CH2:3][CH2:2]1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:27]([C:23]1[CH:22]=[C:21]([CH2:20][N:1]2[CH2:6][CH2:5][CH:4]([C:7]([N:9]3[CH2:18][CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:10]3)=[O:8])[CH2:3][CH2:2]2)[CH:26]=[CH:25][CH:24]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 883945HCID 883945, compound

Product 1

HCID 14499769HCID 14499769, compoundYield 119.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7 g (28.6 mmol) of 2-[(4-piperidyl)carbonyl]-1,2,3,4-tetrahydroisoquinoline, 6.8 g (31.5 mmol) of α-bromo-3-nitrotoluene and 6 g (43 mmol) of potassium carbonate in 140 ml of acetone is stirred for 15 h. The solvent is evaporated off, water and dichloromethane are added and the organic phase is separated off, neutralized, dried and evaporated. 13 g of a yellow oil are obtained, and this is purified by chromatography on a silica column, eluting with a 98:2 dichloromethane/methanol mixture. After recrystallization in ether, 9.6 g of product are obtained, this being used without further purification in the following stage.

Workup

  1. customThe solvent is evaporated off
  2. additionwater and dichloromethane are added
  3. customthe organic phase is separated off
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-76ec1c48803e473a902e7b26866b3551
Source dataset
uspto-grants-1989_12
Patent number
US04885302

Reaction notes

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