Citric Acid → 1-butyl-N,N-dimethyl-4,4-bis(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine 2-hydroxypropane-1,2,3-tricarboxylate

HRID 1011622Notes

Reaction equation

HRID 1011622 reaction equation
[CH2:1]([C:5]1([N:39]([CH3:41])[CH3:40])[CH2:10][CH2:9][C:8]([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[CH3:34])=[CH:31][C:30]([C:35]([F:38])([F:37])[F:36])=[CH:29][CH:28]=3)([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[C:42]([OH:54])(=[O:53])[CH2:43][C:44]([CH2:49][C:50]([OH:52])=[O:51])([C:46]([OH:48])=[O:47])[OH:45]>C(O)C>[OH:45][C:44]([C:46]([OH:48])=[O:47])([CH2:49][C:50]([OH:52])=[O:51])[CH2:43][C:42]([OH:54])=[O:53].[CH2:1]([C:5]1([N:39]([CH3:41])[CH3:40])[CH2:10][CH2:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([C:21]([F:22])([F:24])[F:23])=[CH:15][CH:14]=3)([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[CH3:34])=[CH:31][C:30]([C:35]([F:38])([F:36])[F:37])=[CH:29][CH:28]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 445175681-butyl-N,N-dimethyl-4,4-bis(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine

Product 1

HCID 445175671-butyl-N,N-dimethyl-4,4-bis(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine 2-hydroxypropane-1,2,3-tricarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-butyl-N,N-dimethyl-4,4-bis(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine (100 mg, 0.17 mmol) was dissolved in ethanol (10 ml) and mixed with citric acid (36 mg, 0.187 mmol) dissolved in hot ethanol (3 ml). The clear colourless solution was stirred for 48 h and then concentrated to low volume. After adding diethyl ether (10 ml), the mixture was stirred for 2 h at RT and the precipitate was then aspirated.

Workup

  1. concentrationconcentrated to low volume
  2. additionAfter adding diethyl ether (10 ml)
  3. stirringthe mixture was stirred for 2 h at RT

Sources & evidence

ORD record
ord-7dd5d2d7c7404608aa092da276995103
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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