Acetyl chloride → HCID 22141306, compound

HRID 428876Notes

Reaction equation

HRID 428876 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][OH:21])[CH:13]3[CH:9]2[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]3)[CH:5]=[CH:6][CH:7]=1.C(N([CH2:27][CH3:28])CC)C.[C:29](Cl)(=[O:31])[CH3:30].C(=O)([O-])[OH:34].[Na+]>O1CCCC1>[C:29]([O:21][CH2:20][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:27](=[O:34])[CH3:28])[CH:3]=2)[CH:13]2[CH:9]1[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]2)(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22141155HCID 22141155, compound

Product 1

HCID 22141306HCID 22141306, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of [6-(3-aminophenyl)-3-hexyl-3-azabicyclo[3.1.0]hex-6-yl]methanol (Preparation 94, 0.03 g, 0.09 nmnol) in tetrahydrofuran (2 ml), stirred under nitrogen and cooled to 0° C., was treated with triethylamine (0.03 ml, 0.19 mmol) and acetyl chloride (0.01 ml, 0.17 mmol). The reaction mixture was stirred at room temperature for 3 h, saturated aqueous sodium hydrogen carbonate (50 ml) was added and the product was extracted with ethyl acetate (25 ml×3). The combined organic extracts were dried (Na2SO4) and then concentrated in vacuo. The crude residue was purified on a Sep-Pak™ cartridge packed with silica gel (5 g) to give the product as a clear glass, (11 mg, 34%).

Workup

  1. extractionthe product was extracted with ethyl acetate (25 ml×3)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on a Sep-Pak™ cartridge

Sources & evidence

ORD record
ord-bb0eeed450a54f469ce070431bbee72b
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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