Triethylamine → HCID 12043489, compound

HRID 2184927Notes

Reaction equation

HRID 2184927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][C:18]([NH:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([CH2:34][CH3:35])[C:26]3[C:31]([C:32]=2[CH:33]=1)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:19].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([CH2:16][CH2:17][C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([CH2:34][CH3:35])[C:26]5[C:31]([C:32]=4[CH:33]=3)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:19])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 9968010HCID 9968010, compound

Product 1

HCID 12043489HCID 12043489, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Chlorophenyl)-4-hydroxypiperidine (229 mg, 1.1 mmol, 1.5 equiv) was added in one portion to a solution of 3-bromo-N-(9-ethyl-9H-carbazol-3-yl)-propionamide (250 mg, 0.72 mmol, 1 equiv) and triethylamine (0.301 mL, 219 mg, 2.2 mmol) in DMF (2 mL). The resultant solution was maintained at room temperature for 21 hours and then diluted with ethyl acetate (25 mL). The mixture was washed with water (25 mL) and saturated aqueous sodium chloride (2×25 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by rotary chromatography (5% MeOH/CH2Cl2) to afford 3-[4-(4-chloro-phenyl)-4-hydroxy-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-yl)-propionamide (278 mg, 81%) as a white solid.

Workup

  1. washThe mixture was washed with water (25 mL) and saturated aqueous sodium chloride (2×25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by rotary chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d91b16136ad14aea8db8cb2f2aca1401
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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