Acetonitrile → HCID 131710252, compound

HRID 1657360Notes

Reaction equation

HRID 1657360 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].CC#N.[CH3:12][N:13]([CH3:40])[CH2:14][CH2:15][CH2:16][N:17]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]2[CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[CH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:19]2=[N:18]1.C([O-])(=O)/C=C\C([O-])=O>CCOCC>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:40][N:13]([CH3:12])[CH2:14][CH2:15][CH2:16][N:17]1[CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]2[CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[CH:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:19]2=[N:18]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 444266Maleic AcidHCID 5288227Maleate(2-)HCID 54449379HCID 54449379, compound

Product 1

HCID 131710252HCID 131710252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The base from part (b) and 1.3 g. of maleic acid are dissolved in 25 ml. of warm MeCN and diluted to approximately 600 ml. with ether. On rubbing and standing in the cold, the crystalline maleate salt slowly separates. After four days in the cold, the maleate salt is filtered, washed with ether, and dried in vacuo yielding 4.1 g. (32%); m.p. 109°-111°. Crystallization from 25 ml. methanol-250 ml. ether yields 3.5 g. (27%) of nearly colorless 3a,4,5,6,7,8-hexahydro-N,N-dimethyl-3-phenyl-8-(phenylmethylene)-cyclohepta[c]pyrazole-2(3H)-propanamine, maleate, m.p. 109°-111°.

Workup

  1. filtrationAfter four days in the cold, the maleate salt is filtered
  2. washwashed with ether
  3. customdried in vacuo
  4. customyielding 4.1 g
  5. customCrystallization from 25 ml
  6. customether yields 3.5 g

Sources & evidence

ORD record
ord-e7043bb8e04347a8b4788e3624f457dd
Source dataset
uspto-grants-1976_06
Patent number
US03960848

Reaction notes

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