Water → HCID 69412018, compound

HRID 917683Notes

Reaction equation

HRID 917683 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH:9]([OH:11])[CH2:8][CH2:7][C:6]1([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[CH:14]=1)[OH:12])[CH3:3].[C:25]([Cl:30])(=[O:29])[CH2:26][CH2:27][CH3:28].O>C1COCC1>[ClH:30].[CH3:3][N:2]([CH2:4][CH:5]1[C:6]([OH:12])([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]=2)[CH2:7][CH2:8][CH:9]([O:11][C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH2:10]1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 8855Butyryl chloride2×HCID 69135511HCID 69135511, compound

Product 1

HCID 69412018HCID 69412018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

70.0 g 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexane-1,4-diol were suspended in 560 ml THF p.a., 44.0 g potassium-tert.-butylate added in portions, the mixture stirred for 20 minutes, 21.0 ml butyryl chloride added dropwise, the mixture stirred for a further 20 minutes and a further 21.0 g potassium-tert.-butylate and 20.0 ml butyryl chloride respectively added again twice in accordance with the above model. For working up, 290 ml water were added with ice bath cooling, the phases separated, the mixture extracted once with ethyl acetate, the combined organic phases washed with 1 M sodium hydrogen carbonate solution, dried by magnesium sulphate, filtered and concentrated. 47.1 g of the hydrochloride of butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)cyclohexyl ester were obtained from the crude product obtained (90 g) in the same way as in AAV 1.

Workup

  1. stirringthe mixture stirred for a further 20 minutes
  2. temperaturecooling
  3. customthe phases separated
  4. extractionthe mixture extracted once with ethyl acetate
  5. washthe combined organic phases washed with 1 M sodium hydrogen carbonate solution
  6. dry with materialdried by magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e6b71ec5535b4be9bd694cf05c9311b1
Source dataset
uspto-grants-2007_09
Patent number
US07273952B2

Reaction notes

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