methyl 4-amino-1-benzylpiperidine-4-carboxylate → HCID 22020939, compound

HRID 385778Notes

Reaction equation

HRID 385778 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1([C:21](OC)=[O:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1>C1COCC1>[NH2:7][C:8]1([CH2:21][OH:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 3044632methyl 4-amino-1-benzylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22020939HCID 22020939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 1 L 4-neck round bottom flask was added LAH (9.42 g, 248 mmol) in dry THF (1000 mL) and the reaction mixture was cooled to 0° C. A solution of methyl 4-amino-1-benzylpiperidine-4-carboxylate (47.0 g, 165 mmol) in dry THF (250 ml) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was cooled to 0° C. and quenched with water and filtered. The solid was washed with 50 ml of ethyl acetate. The organic layer of the filtrate was separated, washed with 2×200 ml portions of water and 200 ml of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound.

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with water
  4. filtrationfiltered
  5. washThe solid was washed with 50 ml of ethyl acetate
  6. customThe organic layer of the filtrate was separated
  7. washwashed with 2×200 ml portions of water and 200 ml of brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-445bfa250f244e158b36270e9900faef
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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