Water → 6-Chloro-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine]

HRID 1707117Notes

Reaction equation

HRID 1707117 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[CH2:9][C:10]3([CH2:15][CH2:14][N:13](C#N)[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(O)(=O)/C=C\C(O)=O>O1CCCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[CH2:9][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 444266Maleic AcidHCID 131540506-Chloro-1'-cyano-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine]HCID 21226445Aluminium lithium hydride

Product 1

HCID 128016236-Chloro-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.4 g of 6-chloro-1'-cyano-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine], Example 26, in 50 ml of tetrahydrofuran is added dropwise to a refluxing slurry of 1.0 g of lithium aluminum hydride in 50 ml of tetrahydrofuran. After total addition the mixture is stirred at reflux for 2.5 hours before being treated with water and alkali. The resulting oily product, in ether, is converted to its maleic acid salt which is recrystallized from an ethyl alcohol-ether mixture to provide off-white granules, mp 174.5°-175.5° C. of 6-chloro-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine] meleate.

Workup

  1. additionAfter total addition the mixture
  2. temperatureat reflux for 2.5 hours
  3. customis recrystallized from an ethyl alcohol-ether mixture

Sources & evidence

ORD record
ord-52b6cc80c33e4b2e937b20a61c2a5c09
Source dataset
uspto-grants-1980_06
Patent number
US04209625

Reaction notes

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