Triethylamine → HCID 22405329, compound

HRID 440777Notes

Reaction equation

HRID 440777 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]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38](Cl)=[O:39])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[CH:23]=[CH2:24]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:22]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][C:35]([C:38]([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:39])=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)[CH:23]=[CH2:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14766636HCID 14766636, compoundHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 22405329HCID 22405329, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.3 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 60 ml of dry methylene chloride, under nitrogen, and cooled to 0° C. is added 22.0 ml of triethylamine followed by a solution of 1.2 equivalents of 4'-(2-propenyloxy)-[1,1'-biphenyl]-4-carbonyl chloride in 20 ml of methylene chloride. The reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with 50 ml of chloroform and washed with 50 ml each of water, 2N HCl, water, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and columned on silica gel by elution with 7:1 to 3:1 ethyl acetate:hexane to give 4.8 g of the desired product as a solid. M+H 421.2 M+Na 443.2.

Workup

  1. washwashed with 50 ml each of water, 2N HCl, water, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. washcolumned on silica gel by elution with 7:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-6669fbb77b334c019db90596377d053c
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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