Triethylamine → HCID 15512826, compound

HRID 1978839Notes

Reaction equation

HRID 1978839 reaction equation
[CH2:1]([C@@H:8]([NH:25][CH3:26])[CH2:9][N:10]1[CH2:15][CH2:14][C:13]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])=[CH:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:34]1([C:40](Cl)=[O:41])[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>ClCCl>[CH2:1]([C@@H:8]([N:25]([CH3:26])[C:40]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[O:41])[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[CH2:12][CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 15512827{(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine2×

Product 1

HCID 15512826HCID 15512826, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a N2 atmosphere, a solution of of {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxyphenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine (0.17 g, 0.48 mmole described as intermediate 12 above) and triethylamine (0.15 mL, 1.0 mmole) in dichloromethane (10 mL) was cooled to 0° C. 4-Morpholinecarbonyl chloride (0.06 mL, 0.51 mmole) was added and the resulting mixture was stirred at 0° C. to room temperature (ice melt) overnight. The solvent was evaporated to give a brown residue. Flash chromatography (elution with 7:3 EtOAc-hexane) gave 0.17 g (74% yield) of morpholine-4-carboxylic acid {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydro-4H-pyridin-1-yl]-ethyl}-methyl-amide. An ethanolic solution of the product was heated to gentle reflux and 1 equivalent of fumaric acid in hot ethyl alcohol solution was added to afford the fumarate salt of the titled compound as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customto give a brown residue
  3. washFlash chromatography (elution with 7:3 EtOAc-hexane)

Sources & evidence

ORD record
ord-c919d95366ed410bb78d6f78f963001d
Source dataset
uspto-grants-2001_05
Patent number
US06239126B1

Reaction notes

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