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

HRID 261474Notes

Reaction equation

HRID 261474 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 is added dropwise to a stirred suspension of 6.0 g of 2,3-dihydrospiro[benzofuran-2,4'-piperidine], Example 1C, 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 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 removed under reduced pressure
  6. customleaving a residue which
  7. customThe solid is recrystallized twice from hexane

Sources & evidence

ORD record
ord-cbc26c2cf760444590ea819f9863aaa2
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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