Hydrochloric Acid → (4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

HRID 908918Notes

Reaction equation

HRID 908918 reaction equation
[OH-].[K+].[ClH:3].C[O:5][C:6](=[O:23])[CH:7]=[C:8]1[CH2:13][CH2:12][C:11]([N:20]([CH3:22])[CH3:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.CCOCC.Cl>C(O)C>[ClH:3].[CH3:22][N:20]([CH3:21])[C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13][C:8](=[CH:7][C:6]([OH:23])=[O:5])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 67386135(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester hydrochloride

Product 1

HCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.7 M KOH (70.5 ml, 120 mmol) was added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester hydrochloride (1.8 g, 5.8 mmol) in ethanol (200 ml) and the mixture was stirred at RT for 16 h. The reaction mixture was concentrated and the residue was taken up in water (40 ml). The aqueous phase was extracted by shaking with ether (2×40 ml), and 5.5 M hydrochloric acid (23.6 ml, 130 mmol) was added. After the aqueous phase had been concentrated, the residue was extracted with ethanol (2×40 ml), the potassium chloride which remained was separated off and the filtrate was concentrated. The hydrochloride of the acid was thereby obtained as a colourless solid in a yield of 98% (1.67 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous phase was extracted
  3. additionwas added
  4. concentrationAfter the aqueous phase had been concentrated
  5. extractionthe residue was extracted with ethanol (2×40 ml)
  6. customthe potassium chloride which remained was separated off
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c1b813893309407887b16d63fe4d1012
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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