Triethylamine → HCID 23381013, compound

HRID 2181722Notes

Reaction equation

HRID 2181722 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[CH:22]([CH3:36])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][CH2:33][CH2:34][OH:35])=[CH:27][CH:26]=1.CCN(CC)CC>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:15]2[CH2:16][CH2:17][N:18]([CH2:36][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[C:32][CH2:33][CH2:34][OH:35])=[CH:27][CH:26]=3)[CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668697(-)-1-[(4-Chlorophenyl)phenylmethyl]piperazineHCID 22482228HCID 22482228, compound

Product 1

HCID 23381013HCID 23381013, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1R)(4-chlorophenyl)phenylmethyl]piperazine (1.6 g, 5.6 mmol) and 4-[4(2-bromopropoxy)phenyl]but-3-yn-1-ol (2.0 g, 7.04 mmol) were dissolved in dichloromethane (10 mL). Et3N (1 mL, 7.04 mmol) was added dropwise, the solution was heated at reflux under Ar overnight. The solvent was evaporated and the compound was purified by silica gel chromatography, eluted with ethyl acetate. 2.0 g of the title compound were obtained as a white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux under Ar overnight
  3. customThe solvent was evaporated
  4. customthe compound was purified by silica gel chromatography
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-eb765ff3dd7a4ce3bb97717fd6c0e962
Source dataset
uspto-grants-2005_05
Patent number
US06894059B1

Reaction notes

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