Aluminium lithium hydride → N-methyl-3-(m-trifluoromethylphenyl)-piperidine

HRID 128216Notes

Reaction equation

HRID 128216 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:24])([F:23])[C:9]1[CH:10]=[C:11]([CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH:21]=O)[CH2:16]2)[CH:12]=[CH:13][CH:14]=1>O1CCCC1>[CH3:21][N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:8]([F:7])([F:23])[F:24])[CH:10]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23468751HCID 23468751, compound

Product 1

HCID 3049033N-methyl-3-(m-trifluoromethylphenyl)-piperidineYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7 °C

Procedure

2 g of lithium aluminum hydride were added in small amounts to 100 ml of tetrahydrofuran and the mixture was cooled to 7° C. A solution of 10 g of the product of Step A in 60 ml of tetrahydrofuran was added thereto over about 20 minutes while keeping the temperature at 5° to 10° C. and the mixture was stirred for an hour at room temperature and was then poured into ice. The mixture was stirred for 15 minutes at room temperature and was then filtered. The filtrate was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness to obtain 9.1 g of N-methyl-3-(m-trifluoromethylphenyl)-piperidine in the form of a resin.

Workup

  1. additionwas then poured into ice
  2. stirringThe mixture was stirred for 15 minutes at room temperature
  3. filtrationwas then filtered
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe organic phase was washed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1ccdd9db98204acd991ccae4195ccc19
Source dataset
uspto-grants-1981_03
Patent number
US04259337

Reaction notes

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