Diethyl Ether → 6-Chloro-1-(2-chlorophenyl)-1'-phenoxycarbonylspiro[indoline-3,4'-piperidine]

HRID 1707119Notes

Reaction equation

HRID 1707119 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[CH2:9][C:10]3([CH2:15][CH2:14][N:13](C)[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.C(O)(=O)/C=C\C(O)=O.ClC1C=C2N(C3C=CC=CC=3Cl)CC3(CCN(C)CC3)C2=CC=1.Cl[C:56]([O:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:57].CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([C:56]([O:58][C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)=[O:57])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 15891Phenyl chloroformateHCID 12801625HCID 12801625, compoundHCID 128016266-Chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

Product 1

HCID 204426646-Chloro-1-(2-chlorophenyl)-1'-phenoxycarbonylspiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.8 g of 6-chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine], free base of Example 28, and 0.5 g of phenyl chloroformate in 20 ml of methylene chloride is stirred at ambient temperature for 16 hours. Thereafter, the mixture is successively washed with 10% sodium hydroxide, washed with water, dried and concentrated under vacuum leaving a brownish oil. The oil is passed through an alumina column, ether eluant, providing a colorless gum of 6-chloro-1-(2-chlorophenyl)-1'-phenoxycarbonylspiro[indoline-3,4'-piperidine]. IR and NMR spectra confirm the assigned structure.

Workup

  1. washThereafter, the mixture is successively washed with 10% sodium hydroxide
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customleaving a brownish oil

Sources & evidence

ORD record
ord-7359a1433ccd423692ff4698be7e49e0
Source dataset
uspto-grants-1980_06
Patent number
US04209625

Reaction notes

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