1,1'-Carbonyldiimidazole → 1-(1,4-Benzodioxan-2-yl-acetyl)-4-ethoxy-4-phenylpiperidine

HRID 1391068Notes

Reaction equation

HRID 1391068 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][C:12]([OH:14])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:27]([O:29][C:30]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:28]>O1CCCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][C:12]([N:33]1[CH2:34][CH2:35][C:30]([O:29][CH2:27][CH3:28])([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:31][CH2:32]1)=[O:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2675342,3-Dihydro-1,4-benzodioxin-2-acetic acidHCID 4173924-Ethoxy-4-phenylpiperidinium chloride

Product 1

HCID 213319941-(1,4-Benzodioxan-2-yl-acetyl)-4-ethoxy-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 3.3 g of 1,4-benzodioxan-2-yl-acetic acid in 30 ml of tetrahydrofuran, 3.1 g of 1,1'-carbonyldiimidazole are added while stirring followed, after 30 minutes, by 3.5 g of 4-ethoxy-4-phenylpiperidine in 30 ml of tetrahydrofuran. The mixture is stirred for 18 hours at room temperature, evaporated and the residue taken up in ethyl acetate. The solution is washed with water, N hydrochloric acid and saturated aqueous sodium chloride, dried and evaporated, to yield the 1-(1,4-benzodioxan-2-yl-acetyl)-4-ethoxy-4-phenylpiperidine.

Workup

  1. customThe starting material is prepared
  2. stirringThe mixture is stirred for 18 hours at room temperature
  3. customevaporated
  4. washThe solution is washed with water, N hydrochloric acid and saturated aqueous sodium chloride
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-5b9cef8180d24d8985419b3103e05fe7
Source dataset
uspto-grants-1979_02
Patent number
US04140781

Reaction notes

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