Dimethylformamide → HCID 21939777, compound

HRID 1242876Notes

Reaction equation

HRID 1242876 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][CH:14]([CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:13][CH2:12]2.Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:31][CH:30]=1>C(OCC)(=O)C.O>[C:36]([NH:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:13][CH2:12]3)=[CH:34][CH:33]=1)(=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21939785HCID 21939785, compoundHCID 21939959HCID 21939959, compound

Product 1

HCID 21939777HCID 21939777, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oily, 85 mg) was added to DMF solution of 6-hydroxy-2-(2-piperidinoethyl)tetralin (500 mg) at room temperature, which was stirred for 1 hour. N-[4-(bromomethyl)phenyl]benzamide (670 mg) was added to the reaction mixture at room temperature, which was stirred for 1 hour. Water was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: THF), and recrystallized (ethyl acetate) to give the titled compound (200 mg).

Workup

  1. stirringwhich was stirred for 1 hour
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customrecrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-628975a7cd0c468cb5fecef2651549ab
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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