4-(1-Pyrrolidinyl)piperidine → HCID 10187539, compound

HRID 1270193Notes

Reaction equation

HRID 1270193 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]4[C:24]([C:27](Cl)=[O:28])=[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.C1(C2C=C[C:41]([C:42]([N:44]3[C:50]4C=CC=C[C:49]=4[CH2:48][N:47]4[C:55](C(O)=O)=[CH:56][CH:57]=[C:46]4C3)=O)=CC=2)CCCCC1.N1(C2CCNCC2)CCCC1.C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[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]4[C:24]([C:27]([N:44]5[CH2:42][CH2:41][CH:48]([N:47]6[CH2:46][CH2:57][CH2:56][CH2:55]6)[CH2:49][CH2:50]5)=[O:28])=[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

Participants

7

Reactant 4

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 81531DiisopropylethylamineHCID 10223535HCID 10223535, compoundHCID 18449085HCID 18449085, compound

Product 1

HCID 10187539HCID 10187539, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of the crude 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl chloride (prepared in the manner of Example 23, from 1 g of the corresponding carboxylic acid of Example 22) in dichloromethane (25 mL) was treated with 4-(1-pyrrolidinyl) piperidine (0.74 g), N,N-diisopropylethyl amine (0.31 g) and 4-(dimethylamino)pyridine (0.05 g). The reaction mixture was stirred at room temperature overnight, washed with water and saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. Filtration of this solution through a short column of Magnesol® gave a pale yellow eluate which was evaporated to dryness to provide the title compound as a pale yellow amorphous material (0.42 g).

Workup

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration of this solution through a short column of Magnesol®
  4. customgave a pale yellow eluate which
  5. customwas evaporated to dryness

Sources & evidence

ORD record
ord-22b9044df12a4ecabc876a659477356e
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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