Aluminium lithium hydride → HCID 43585737, compound

HRID 524862Notes

Reaction equation

HRID 524862 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH:17]([N:20]([CH3:28])[C:21](=O)OC(C)(C)C)[CH2:16][CH2:15]1>C1COCC1>[CH3:21][N:20]([CH3:28])[CH:17]1[CH2:16][CH2:15][N:14]([C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH2:7])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86720919HCID 86720919, compound

Product 1

HCID 43585737HCID 43585737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of LiAlH4 (49.57 mg, 1.306 mmol) was added dropwise to a solution of tert-butyl N-[1-(3-amino-4-pyridyl)-4-piperidyl]-N-methyl-carbamate (100 mg, 0.3264 mmol) in THF at room temp. The reaction was stirred at 50° C. for 3 h, then at room temperature, the reaction mixture was quenched by the dropwise addition of wet THF. The reaction mixture was partitioned between 1N NaOH (50 mL) and diethyl ether (50 mL). The combined organics was dried (MgSO4) and evaporated to leave 4-(4-(dimethylamino)piperidin-1-yl)pyridin-3-amine as a yellow oil. MS (ES+) 221.1.

Workup

  1. customat room temperature, the reaction mixture was quenched by the dropwise addition of wet THF
  2. customThe reaction mixture was partitioned between 1N NaOH (50 mL) and diethyl ether (50 mL)
  3. dry with materialThe combined organics was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9fe977707a1b4eee94586842aa4b250e
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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