Acetyl chloride → 2,3-Dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine]

HRID 261499Notes

Reaction equation

HRID 261499 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[CH2:10][CH2:9][C:8]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:7][CH2:6]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([N:5]1[CH2:10][CH2:9][C:8]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 127332303H-Spiro(1-benzofuran-2,4'-piperidine)

Product 1

HCID 127332342,3-Dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3 ml of acetyl chloride in 10 ml of chloroform are added dropwise to a stirred suspension of 6.0 g of 2,3-dihydrospiro[benzofuran-2,4'-piperidine], Example 7, and 14.0 g of sodium bicarbonate in 75 ml of chloroform. After total addition, the reaction mixture is successively stirred at ambient temperature for 16 hours, filtered, washed sequentially with water, dilute hydrochloric acid and a saturated sodium chloride solution, dried and the solvent is removed under reduced pressure, leaving a residue which solidifies upon standing. The solid is recrystallized twice from hexane to give the product, 2,3-dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine], mp 94°-97° C.

Workup

  1. additionAfter total addition
  2. filtrationfiltered
  3. washwashed sequentially with water, dilute hydrochloric acid
  4. dry with materiala saturated sodium chloride solution, dried
  5. customthe solvent is removed under reduced pressure
  6. customleaving a residue which
  7. customThe solid is recrystallized twice from hexane

Sources & evidence

ORD record
ord-bf4304d8b0344aa49324e93f937d7992
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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