Morpholine → HCID 24900204, compound

HRID 1819879Notes

Reaction equation

HRID 1819879 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:9]2[O:10][C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:8]=2[CH:7]=1)=[O:4].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N:20]1([CH2:2][C:3]([NH:5][C:6]2[CH:19]=[CH:18][C:9]3[O:10][C:11]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[C:8]=3[CH:7]=2)=[O:4])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 24900205HCID 24900205, compound

Product 1

HCID 24900204HCID 24900204, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.13 g, 0.45 mmol), morpholine (0.049 mL, 0.56 mmol), and cesium carbonate (0.29 g, 0.90 mmol) in acetonitrile (5 mL) was stirred overnight at room temperature. The reaction mixture was concentrated and the crude material was purified using reverse-phase HPLC to provide 2-morpholin-4-yl-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.085 g). MS (ESI) m/z 329 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was purified

Sources & evidence

ORD record
ord-c94aa796f212456c8d669c80ede12a7b
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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