Triethylamine → 4-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-N-propyl-N-(prop-2-ynyl)-butyramide

HRID 2399702Notes

Reaction equation

HRID 2399702 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH2:11][CH2:10]1.C(N(CC)CC)C.O=C1N(N(N2CCOC2=O)P(Cl)(Cl)=O)CCO1.[CH2:51]([NH:54][CH2:55][C:56]#[CH:57])[CH2:52][CH3:53]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([N:54]([CH2:55][CH2:56][CH3:57])[CH2:51][C:52]#[CH:53])=[O:19])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4724212(Prop-2-yn-1-yl)(propyl)amineHCID 98634284-[4-(2-Methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acidHCID 19975454N,N-bis(2-oxo-3oxazolidinyl)phosphoramidic chloride

Product 1

HCID 152963764-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-N-propyl-N-(prop-2-ynyl)-butyramideYield 11.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid (1.772 g, 5 mmole), triethylamine (1.518 g, 15 mmole), and N,N-bis(2-oxo-3-oxazolidinyl)phosphoramidic chloride (1.527 g, 6 mmole) was stirred in methylene chloride (80 mL) under exclusion of moisture at ambient temperature for 30 minutes, after which N-propylpropargylamine (0.804 g, 6 mmole) was added at once at 0° C. The reaction mixture was stirred at room temperature overnight, washed with water (2×100 mL), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Chromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether with addition of ethanolic hydrochloric acid gave 0.25 g of the title compound as the dihydrochloride sesquihydrate, m.p. 172°-4° C.

Workup

  1. washwashed with water (2×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness in vacuo
  5. additionChromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether with addition of ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-70a18441bad74d269fe62515cfff4f9e
Source dataset
uspto-grants-1995_09
Patent number
US05451584

Reaction notes

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