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

HRID 1660355Notes

Reaction equation

HRID 1660355 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:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>O1CCCC1.CCOCC>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[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 128016246-Chloro-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine] maleate

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] maleate.

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-e84267c525ec4855823a08ca73216539
Source dataset
uspto-grants-1981_12
Patent number
US04307235

Reaction notes

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