Triethylamine → {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine

HRID 1633583Notes

Reaction equation

HRID 1633583 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:27][CH3:28])=[C:7]([C:9]2[CH2:10][CH2:11][N:12]([C:15](=O)[C@H:16]([NH:24][CH3:25])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH:14]=2)[CH:8]=1.C(N(CC)CC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:17]([C@@H:16]([NH:24][CH3:25])[CH2:15][N:12]1[CH2:13][CH2:14][C:9]([C:7]2[CH:8]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=2[O:27][CH3:28])=[CH:10][CH2:11]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21226445Aluminium lithium hydrideHCID 69692845HCID 69692845, compound

Product 1

HCID 15512827{(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2R)-1-[4-(5-fluoro-2-methoxy-phenyl)-1,2,3,6-tetrahydropyridin-1-yl]-2-methylamino-3-phenyl-propan-1-one hydrochloride (0.41 g, 1.0 mmole) in 20 mL of tetrahydrofuran at 0° C. under N2 was added of triethylamine (0.14 mL, 1.0 mmol), followed by slow addition of 1.9 mL (1.9 mmole) lithium aluminum hydride (1 M solution in THF). After addition, the cooling bath was removed and the mixture was stirred at room temperature for 2.5 hours. The reaction was quenched by the slow addition of saturated NH4Cl solution and the mixture was filtered through a celite pad. The solution was concentrated to afford 0.36 g (100% {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine as a yellow oil which was used without further purification.

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. customThe reaction was quenched by the slow addition of saturated NH4Cl solution
  4. filtrationthe mixture was filtered through a celite pad
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-cf22e7ae1c254f85829b5576c0e5fbde
Source dataset
uspto-grants-2003_01
Patent number
US06503928B2

Reaction notes

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