Water → HCID 21887736, compound

HRID 2374594Notes

Reaction equation

HRID 2374594 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:22]=[CH:21][C:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:14]=2[CH:13]=1)=[O:11].C(N(CC)CC)C.O>O1CCCC1>[C:1]([N:18]1[CH2:17][CH2:16][C:15]2[CH:21]=[CH:22][C:12]([C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][Cl:5])=[CH:13][C:14]=2[CH2:20][CH2:19]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21887245HCID 21887245, compound

Product 1

HCID 21887736HCID 21887736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (679 μl) was added to a solution of 5-chloro-1-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1-pentanone (2.2 g) obtained in Reference Example 121 and triethylamine (1.67 ml) in tetrahydrofuran (30 ml). After stirring at room temperature for 60 minutes, water (50 g) was added, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give an oil (2.54 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e4213553fee446ada1bcf2cf8777bdb2
Source dataset
uspto-grants-2008_12
Patent number
US07462628B2

Reaction notes

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