Dimethylamine → HCID 22405325, compound

HRID 440772Notes

Reaction equation

HRID 440772 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:27]=[CH:26][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][N:15]3[CH:23]=[CH:24][CH:25]=[C:14]3[CH2:13]2)=[O:11])=[CH:8][CH:7]=1.[CH2:28]=O.[CH3:30][NH:31][CH3:32].CO>O1CCCC1>[CH3:30][N:31]([CH2:28][C:23]1[N:15]2[C:14]([CH2:13][N:12]([C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[CH:27][CH:26]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16]2)=[CH:25][CH:24]=1)[CH3:32]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 887MethanolHCID 15298022HCID 15298022, compound

Product 1

HCID 22405325HCID 22405325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 400 mg of 10,11-dihydro-10-[4-(2-thienyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 10 ml of 40% formalin and 10 ml of 40% N,N-dimethylamine in 50 ml of 1:1 tetrahydrofuran:methyl alcohol is refluxed for 3 hours. The reaction mixture is evaporated in vacuo to a residue which is extracted with chloroform, washed with water, dried over Na2SO4, filtered and the filtrate evaporated in vacuo to give a residue which is purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane to give 300 mg of the desired product as a solid. Mass spectrum: M+H:428.

Workup

  1. customThe reaction mixture is evaporated in vacuo to a residue which
  2. extractionis extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customto give a residue which
  8. customis purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-75d77315f5d34e9db96881fba51bbddf
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

Loading…