Diisopropylethylamine → HCID 19776689, compound

HRID 1612831Notes

Reaction equation

HRID 1612831 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:22][C:23]#[C:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34].C(N(CC)C(C)C)(C)C>ClCCl>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:22][C:23]#[C:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:33]([O-:35])=[O:34])[CH2:11][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 30175844-BenzhydryloxypiperidineHCID 13100667HCID 13100667, compound

Product 1

HCID 19776689HCID 19776689, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 35 ml of dichloromethane were dissolved 2.67 g of 4-diphenylmethoxypiperidine, 2.93 g of 1-chloro-4-(2-nitrophenoxy)-2-butyne and 1.68 g of N,N-diisopropylethylamine, and the resultant solution was stirred at room temperature for 20 hours. The reaction solution was washed with water, and the solvent was removed under reduced pressure. The residue was eluted with ethyl acetate by silica gel column chromatography to give 2.95 g of oily 4-diphenylmethoxy-1-[4-(2-nitrophenoxy)-2-butynyl]piperidine.

Workup

  1. washThe reaction solution was washed with water
  2. customthe solvent was removed under reduced pressure
  3. washThe residue was eluted with ethyl acetate by silica gel column chromatography

Sources & evidence

ORD record
ord-d50a33d872ff4435895237ee028afa44
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

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