HCID 23105847, compound → HCID 23105725, compound

HRID 917682Notes

Reaction equation

HRID 917682 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([OH:12])[CH2:9][CH:8]=[C:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH3:4].[Cl:21][Si](C)(C)C>CC(=O)CC.O>[ClH:21].[CH3:4][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([OH:12])[CH2:9][CH:8]=[C:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH3:2]

Participants

4

Reactant 1

HCID 23105847HCID 23105847, compound

Product 1

HCID 23105725HCID 23105725, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

20.0 g 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol (equatorial alcohol) were dissolved in 300 ml concentrated formic acid, 6.75 ml acetyl chloride were added and the mixture heated for two hours to reflux. After cooling the mixture was concentrated, the residue taken up with 2 M sodium hydroxide solution and extracted with ethyl acetate. The combined extracts were dried by sodium sulphate, filtered, concentrated, the crude product obtained (16.7 g) dissolved in 2-butanone and by addition of 1.15 ml water and 8.1 ml chlorotrimethylsilane 5-dimethylaminomethyl-4-(3-methoxyphenyl)-cyclohex-3-enol hydrochloride (17.7 g) precipitated.

Workup

  1. customprecipitated

Sources & evidence

ORD record
ord-cbe5078ee5184b4390f6f94289eb97ad
Source dataset
uspto-grants-2007_09
Patent number
US07273952B2

Reaction notes

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