1,2-Dichloroethane → 1-[4-(5,6,7,8-Tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)piperidin-1-yl]-ethanone

HRID 1839663Notes

Reaction equation

HRID 1839663 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:27]1[C:36]2[CH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:30]=2[CH:29]=[CH:28]1>C(Cl)Cl>[NH:27]1[C:36]2[CH2:35][CH2:34][CH2:33][CH2:32][N:31]([C:10]([CH:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)=[O:12])[C:30]=2[CH:29]=[CH:28]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1172551-Acetylpiperidine-4-carboxylic acidHCID 225617901,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepine

Product 1

HCID 225618581-[4-(5,6,7,8-Tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)piperidin-1-yl]-ethanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-acetyl-piperidine-4-carboxylic acid (822 mg, 4.8 mmol, 1.2 eq.), EDC (920 mg, 1.2 eq.), HOBt (648 mg, 1.2 eq.) in DCM (15 mL) was added TEA (1.3 mL, 2 eq.) and 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine (550 mg, 4 mmol). The mixture was stirred at rt for 2 days. The reaction was diluted with DCM, washed with water, sat. NaHCO3, brine, dried and concentrated. The residue was purified on a silica gel column to give 1.1 g of 1-[4-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-piperidin-1-yl]-ethanone as a white solid.

Workup

  1. washwashed with water, sat. NaHCO3, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-8bc9c4c623ba45388ecb9f1a0f860bdc
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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