Aluminium lithium hydride → 3-(1-Methyl-4-piperidinyl)benzenamine

HRID 2375913Notes

Reaction equation

HRID 2375913 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH3:14][N:11]1[CH2:12][CH2:13][CH:8]([C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 223301453-(1-Methyl-4-piperidinyl)benzenamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dried flask was charged with tert-butyl 4-(3-aminophenyl)piperidine-1-carboxylate (0.553 g, 2.00 mmol). Lithium aluminium hydride (1M in THF, 10 mL, 10.0 mmol) was added slowly through a syringe under N2. The resulting mixture was stirred overnight at rt. Water (0.5 mL) was cautiously added to quench the reaction. The resulting mixture was filtered. The filtrate was concentrated to dryness to give the title compound as a white solid, which was used without further purification in the next step. 1H-NMR (CDCl3, 400 MHz): δ=1.80-1.85 (m, 2H), 2.04 (dt, J=4.0, 11.6 Hz, 2H), 2.33 (s, 3H), 2.40 (m, 1H), 2.98 (m, 2H), 3.64 (s, br, 2H), 6.54-6.59 (m, 2H), 6.66 (d, J=7.6 Hz, 1H), 7.10 (t, J=7.6 Hz, 1H). MS (ES+): m/z 191.26 [MH+]. HPLC: tR=0.49 min (ZQ2000, polar—5 min).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe resulting mixture was filtered
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5935e890e57b43f291f0e02c9daa3b44
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…