Ammonium Chloride → HCID 20523634, compound

HRID 1703160Notes

Reaction equation

HRID 1703160 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][C:16]([CH3:22])([CH3:21])[C:17]2=[O:20])=[CH:13][CH:12]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][C:16]([CH3:22])([CH3:21])[C:17]2([CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)[OH:20])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 205236396-Chloro-2,3-dihydro-2,2-dimethyl-1H-inden-1-one

Product 1

HCID 20523634HCID 20523634, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent is prepared from 14.0 g 4-chloro-N-methylpiperidine and 2.6 g magnesium in 200 ml boiling tetrahydrofuran. After cooling, a solution of 10.0 g 6-chloro-2,2-dimethyl-indanone in 50 ml tetrahydrofuran is added dropwise at 5°-10°, and the reaction mixture is refluxed for 6 hours. After cooling, a 10% aqueous solution of ammonium chloride is added and the mixture is extracted with toluene. The toluene phase is dried and evaporated, to give 6-chloro-2,2-dimethyl-1-(1-methyl-4-piperidinyl)indan-1-ol (m.p. 181°-182°).

Workup

  1. temperatureAfter cooling
  2. temperaturethe reaction mixture is refluxed for 6 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with toluene
  5. dry with materialThe toluene phase is dried
  6. customevaporated

Sources & evidence

ORD record
ord-4b95a150837b4792bce825debdffe4e3
Source dataset
uspto-grants-1982_09
Patent number
US04351838

Reaction notes

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