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

HRID 464247Notes

Reaction equation

HRID 464247 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-7aed139ccebf4d788d7654bf96a49045
Source dataset
uspto-grants-1985_10
Patent number
US04547497

Reaction notes

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