Aluminium lithium hydride → ({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amine

HRID 564570Notes

Reaction equation

HRID 564570 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23](OC(C)(C)C)=O)[CH2:19][CH2:18]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:23][N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][C:12]2[CH:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][NH2:2])[CH:5]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 670057291,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate Hydrochloride

Product 1

HCID 57813254({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amineYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1,1-dimethylethyl 4-{[3′-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate hydrochloride (1.23 g, 2.95 mmol) was added LiAlH4 (5.90 mL, 1N in THF, 5.90 mmol) and the reaction was stirred at room temperature until the was complete per monitoring with LC-MS. The reaction mixture was diluted with Et2O (50 mL) and quenched with Na2CO3 (saturated aqueous), filtered, concentrated and purified with Combiflash chromatograph to afford 0.59 g (68%) of the title compound. LC-MS m/z 295 (M+H)+.

Workup

  1. customquenched with Na2CO3 (saturated aqueous)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified with Combiflash chromatograph

Sources & evidence

ORD record
ord-186aeb6004fd4c17bf2c74b668952924
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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