Water → HCID 18348171, compound

HRID 2267965Notes

Reaction equation

HRID 2267965 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH:20]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]1)=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][N:14]1[CH2:15][CH2:16][N:17]([CH:20]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:18][CH2:19]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18348179HCID 18348179, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18348171HCID 18348171, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1.5 grams (0.003 mole) of N-(2-methylindol-3-ylacetyl)-N′-[bis(4-fluorophenyl)methyl]piperazine in 10.0 mL of anhydrous tetrahydrofuran was added to a stirred mixture of 0.4 gram (0.010 mole) of lithium aluminum hydride in 5.0 mL of anhydrous tetrahydrofuran. Upon completion of the addition the reaction mixture was heated to reflux, where it stirred for 2.5 hours. The reaction mixture was cooled to 0° C., and water was added, followed by 50 mL of aqueous 10% sodium hydroxide. The solution was warmed to ambient temperature and then extracted with ethyl acetate. The extract was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.7 gram of N-(2-methylindol-3-ylethyl)-N′-[bis(4-fluorophenyl)methyl]piperazine, mp 65-73° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux
  4. temperatureThe solution was warmed to ambient temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b1d4d8bce70a447ab5ff6053cd0e51c4
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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