Diisopropylethylamine → HCID 10178894, compound

HRID 1826674Notes

Reaction equation

HRID 1826674 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.C(N(CC)C(C)C)(C)C.[CH:26]1([C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>ClCCl>[CH:26]1([C:32]2[CH:33]=[CH:34][C:35]([C:36]([N:5]3[CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:2]([CH3:1])[C:3]4[CH:16]=[CH:15][CH:14]=[CH:13][C:4]3=4)=[O:37])=[CH:39][CH:40]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 218908474-Cyclohexylbenzoyl chlorideHCID 2213523710,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepine

Product 1

HCID 10178894HCID 10178894, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10,11-dihydro-5-methyl-dibenzo[b,e][1,4]diazepine of Step C (0.42 g) in dichloromethane (10 mL) containing N,N-diisopropylethyl amine (0.29 g) was treated with 4-cyclohexylbenzoyl chloride (0.50 g). After stirring overnight at room temperature, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate, then dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. Evaporation of all volatiles gave a glassy residue which was triturated with anhydrous diethyl ether to provide the title compound as an off-white crystalline solid (0.66 g), m.p. 111–112° C.

Workup

  1. washthe reaction mixture was washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered through a short column of Magnesol® which
  4. washwas eluted with several additional volumes of dichloromethane
  5. customEvaporation of all volatiles
  6. customgave a glassy residue which
  7. customwas triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-d8adca14560d4ca0af74cf25c8665c83
Source dataset
uspto-grants-2006_05
Patent number
US07053083B2

Reaction notes

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