Triethylamine → HCID 23381013, compound

HRID 1280448Notes

Reaction equation

HRID 1280448 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-43ab2d82ef8f4d8ab9611e036e43b319
Source dataset
uspto-grants-2002_09
Patent number
US06451801B1

Reaction notes

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