O-Xylene → 12-(4-n-Butyl-1-piperazinyl)-6H-indolo[2,1-c][1,4]benzodiazepine (E)-2-butenedioate

HRID 279850Notes

Reaction equation

HRID 279850 reaction equation
CS[C:3]1[C:9]2=[CH:10][C:11]3[C:16]([N:8]2[CH2:7][C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[N:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.C1(C)C(C)=[CH:23][CH:24]=[CH:25][CH:26]=1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>CCOC(C)=O>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH2:26]([N:4]1[CH2:32][CH2:31][N:8]([C:3]2[C:9]3=[CH:10][C:11]4[C:16]([N:8]3[CH2:7][C:6]3[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=3[N:4]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:9][CH2:3]1)[CH2:25][CH2:24][CH3:23]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 444972Fumaric AcidHCID 1350573612-methylthio-6H-indolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 13171437812-(4-n-Butyl-1-piperazinyl)-6H-indolo[2,1-c][1,4]benzodiazepine (E)-2-butenedioate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7.1 g of 12-methylthio-6H-indolo[2,1-c][1,4]benzodiazepine, the product of Example 1c, 6.64 g of 4-n-butyl-1-piperazine and 20 ml of xylene in a pressure bottle was heated to 240° C. for 3 hours. The reaction mixture was dissolved in EtOAc, washed with water, and dried anhydrous over Na2SO4. The crude product (after removal of solvent) was dissolved in MeOH and treated with one equivalent of fumaric acid to give a solid. Recrystallization of the fumarate salt from DMF yielded the title compound, a colorless solid, mp 197° C. (dec).

Workup

  1. washwashed with water
  2. dissolutionThe crude product (after removal of solvent) was dissolved in MeOH
  3. customto give a solid
  4. customRecrystallization of the fumarate salt from DMF

Sources & evidence

ORD record
ord-b8bae7d4826942dcb780867ae1005339
Source dataset
uspto-grants-1986_05
Patent number
US04587244

Reaction notes

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