1-Methylpiperazine → HCID 10141567, compound

HRID 1270192Notes

Reaction equation

HRID 1270192 reaction equation
[CH:1]1([C:7]2[CH:31]=[CH:30][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4C(C(O)=O)=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:32](Cl)(=[O:36])[C:33](Cl)=O.C(N(CC)C(C)C)(C)C.[CH3:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>ClCCl>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:33]([C:32]([N:51]5[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]5)=[O:36])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:30][CH:31]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 10223535HCID 10223535, compound

Product 1

HCID 10141567HCID 10141567, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Example 22 (3.14 g) in dichloromethane (25 mL) was added oxalyl chloride (3.0 g). The reaction mixture was stirred for five hours at room temperature and then evaporated to dryness. The crude acid chloride thus obtained was dissolved in dichloromethane (50 mL) and added to a mixture of N,N-diisopropylethyl amine (1.0 g) and N-methyl piperazine (1.52 g) in dichloromethane (50 mL). The mixture was stirred at room temperature overnight, then washed with water and saturated aqueous sodium bicarbonate. The solution was dried over anhydrous sodium sulfate and then filtered through a short column of Magnesol®. Removal of the solvent followed by the addition of diethyl ether provided the title compound (2.50 g) as a pale yellow solid, m.p. 134–136° C.

Workup

  1. customevaporated to dryness
  2. customThe crude acid chloride thus obtained
  3. stirringThe mixture was stirred at room temperature overnight
  4. washwashed with water and saturated aqueous sodium bicarbonate
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of Magnesol®
  7. customRemoval of the solvent
  8. additionfollowed by the addition of diethyl ether

Sources & evidence

ORD record
ord-4cd8a7868718422588999acf2c805cae
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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