Triethylamine → HCID 9967998, compound

HRID 433133Notes

Reaction equation

HRID 433133 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[NH:23]1[CH2:28][CH:27]=[C:26]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)[CH2:25][CH2:24]1.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[O:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH:13]1[CH2:12][N:23]1[CH2:24][CH:25]=[C:26]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 9858183HCID 9858183, compound

Product 1

HCID 9967998HCID 9967998, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (0.311 g, 0.98 mmol) in methyl sulfoxide (20 mL) was added 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.500 g, 2.52 mmol) and triethylamine (0.318 g, 3.14 mmol) and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was allowed to cool to room temperature and was diluted with ethyl acetate (200 mL), washed with water (3×100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, methanol:dichloromethane 1:19) provided 0.180 g (58%) of 3-[1-(3,4-dihydro-2H-chromen-2-ylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole as a pale yellow solid. mp 171-173° C.; Anal. Calcd. for C23H24N2O: C, 80.20; H, 7.02; N, 8.13. Found: C, 79.97; H, 7.02; N, 8.14.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water (3×100 mL), aqueous sodium chloride (100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customto give a crude solid
  6. customPurification by flash column chromatography (silica, methanol:dichloromethane 1:19)

Sources & evidence

ORD record
ord-9bfc5a3c26fc4cd6bf616b7ad250431d
Source dataset
uspto-grants-2003_12
Patent number
US06667322B2

Reaction notes

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