2-Bromoethanol → 1-[2-(4-Chlorophenyl)ethyl]piperazine

HRID 1769008Notes

Reaction equation

HRID 1769008 reaction equation
NC1C=CC(C([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=O)=CC=1.CC1OC(OC2C3C(=C(O)C4C(=O)C5C=CC=C(OC)C=5C(=O)C=4C=3O)CC(O)(C(CO)=O)C2)CC(N2C(C#N)COCC2)C1O.BrCCO>CN(C)C1C=CN=CC=1.C(O)(C)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 100184MRA-CN isomer a, a:b = 93:7HCID 189463571-(4-Aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolvent

Procedure

6 g of 1-(4-aminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]-piperazine (see EP-A-489 690, Example 3), 2.4 g of 2-bromoethanol and 0.6 g of 4-dimethylaminopyridine are suspended in 80 ml of isopropanol and boiled at reflux for 22 hours, then concentrated by evaporation and partitioned between methylene chloride and 1N sodium hydroxide solution. The organic phase is washed with water, dried and concentrated by evaporation. The oily material is chromatographed over 150 g of silica gel. Elution with methylene chloride/methanol (100:4 and 100:5) yields 1-[4-N-(2-hydroxyethyl)-amino]-benzoyl]-4-[2-(4-chlorophenyl)-ethyl]-piperazine, m.p. 94°-95°.

Workup

  1. temperatureat reflux for 22 hours
  2. concentrationconcentrated by evaporation
  3. custompartitioned between methylene chloride and 1N sodium hydroxide solution
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe oily material is chromatographed over 150 g of silica gel
  8. washElution with methylene chloride/methanol (100:4 and 100:5)

Sources & evidence

ORD record
ord-631d7f33331e4f469622d665c69eb25c
Source dataset
uspto-grants-1995_01
Patent number
US05380726

Reaction notes

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