Ammonium Chloride → HCID 21435172, compound

HRID 2398294Notes

Reaction equation

HRID 2398294 reaction equation
[CH3:1][CH:2]1[C:11](=[O:12])[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[C:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:4]2[CH:20]=[CH:21][CH:22]=[CH:23][C:3]1=2.[CH3:24][Li].[Cl-].[NH4+]>C1C=CC=CC=1.C(OCC)C>[CH3:1][CH:2]1[C:11]([CH3:24])([OH:12])[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)[C:4]2[CH:20]=[CH:21][CH:22]=[CH:23][C:3]1=2

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21435163HCID 21435163, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 21435172HCID 21435172, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 11.0 g of 9-methyl-4-(1-methyl-4-piperidylidene)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen10(9H)-one in 150 ml of benzene was added dropwise in a nitrogen atmosphere at 25°-30° to a solution of 150 ml of diethylether and 43 ml of 2 molar methyllithium in diethylether. The reaction mixture was stirred for 3 hours at room temperature and then treated with 500 ml of 20% w/v aqueous ammonium chloride. The organic phase was separated off and worked up to give solid 9,10-dihydro9,10-dimethyl-4-(1-methyl-4-piperidylidene)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-ol which was further reacted in crude form.

Workup

  1. additiontreated with 500 ml of 20%
  2. customThe organic phase was separated off

Sources & evidence

ORD record
ord-83eea3810a2b4064bc7bf02fe7ba54e3
Source dataset
uspto-grants-1977_05
Patent number
US04024266

Reaction notes

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