Triethylamine → HCID 22405322, compound

HRID 440782Notes

Reaction equation

HRID 440782 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[CH2:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[CH2:23][CH3:24]>C(Cl)Cl>[CH2:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14985095HCID 14985095, compoundHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 22405322HCID 22405322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 30 ml of methylene chloride, under nitrogen, while cooling to 0° C. is added dropwise 30 ml of triethylamine followed by a solution of 4'-(propyl)[1,1'-biphenyl]-4-carbonyl chloride in 10 ml of methylene dichloride. The reactants are stirred at room temperature for 16 hours. The reaction mixture is poured in ice water and extracted with methylene chloride (3×50 ml) The organic layer is, washed with water, 2N citric acid, saturated aqueous NaHCO3, water and dried (MgSO4) and evaporated in vacuo to give a residue which is purified by column chromatography on silica gel with ethyl acetate-hexane to give 1.4 g of the desired product as a crystalline solid, m.p. 118°-120° C. MS(M+H=407.3; M+Na=429.3)

Workup

  1. extractionextracted with methylene chloride (3×50 ml) The organic layer
  2. washwashed with water, 2N citric acid, saturated aqueous NaHCO3, water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give a residue which
  6. customis purified by column chromatography on silica gel with ethyl acetate-hexane

Sources & evidence

ORD record
ord-903ab17af4e748d1bd9e133ce898106e
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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