Acetyl chloride → 2-[4-(6-Fluoro-1,2-benzisoxazol-yl)-piperidinyl]ethyl acetamide fumarate

HRID 1449933Notes

Reaction equation

HRID 1449933 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]N)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:20]([N:22](CC)CC)[CH3:21].C(Cl)(=[O:29])C.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>C(Cl)Cl.C(O)C>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:21][C:20]([NH2:22])=[O:29])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 444972Fumaric AcidHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 867482572-[4-(6-Fluoro-1,2-benzisoxazol-yl)-piperidinyl]ethyl acetamide fumarate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.56 g, 9.7 mmol) and triethylamine (1.45 g, 14.5 mmol) in DCM (50 ml) was treated with dropwise addition of acetyl chloride (1.0 g, 12.7 mmol) at room temperature. The mixture was stirred for 4 hours at room temperature. The reaction mixture was diluted with DCM and washed with brine. The organic solution was dried over MgSO4 and concentrated to a crude oil. The crude oil was purified by flash chromatography over a silica gel column (SiO2, 20 g; eluted with (0-2%) CH3OH in DCM). The pure product thus obtained weighed 1.36 g (46%). It was converted to a fumarate salt by treatment with fumaric acid (517 mg) in ethanol. Recrystallization from ethanol gave white crystals; weight: 1.53 g, m.p.=132°-133° C. ANALYSIS: Calculated for C16H20FN4O2.C4H4O4 : 57.00%C 5.74%H 9.97%N Found: 57.05%C 5.85%H 9.95%N

Workup

  1. washwashed with brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated to a crude oil
  4. customThe crude oil was purified by flash chromatography over a silica gel column (SiO2, 20 g; eluted with (0-2%) CH3OH in DCM)
  5. customThe pure product thus obtained
  6. customRecrystallization from ethanol
  7. customgave white crystals

Sources & evidence

ORD record
ord-2947fa24c2244af9948c2eb3025efad2
Source dataset
uspto-grants-1997_02
Patent number
US05599821

Reaction notes

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