1-Butanol → HCID 21830772, compound

HRID 1600658Notes

Reaction equation

HRID 1600658 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[N:5][N:4]([CH2:9][CH2:10][CH2:11][CH2:12]Cl)[C:3]1=[O:14].[Cl:15][C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1.C(O)CCC>C(N(CC)CC)C>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[N:5][N:4]([CH2:9][CH2:10][CH2:11][CH2:12][N:25]2[CH2:24][CH2:23][N:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=3)[CH2:27][CH2:26]2)[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 13551-(3-Chlorophenyl)piperazineHCID 29928023HCID 29928023, compound

Product 1

HCID 21830772HCID 21830772, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The compound 4c (5.5 g; 0.025 mol) and 4-(3-chlorophenyl)piperazine (9.83 g; 0.05 mol) are heated for 3 hours in refluxing butanol (150 ml) in the presence of triethylamine (10 ml). The mixture is concentrated to dryness under vacuum, taken up in water and then extracted with ethyl ether (2×50 ml). The dried organic phases (Na2SO4) are concentrated to dryness under vacuum to give an oil which crystallizes from isopropyl ether (70 ml). After recrystallization from 2-propanol and drying under vacuum at 40° C., the compound 4 (4.24 g) is obtained.

Workup

  1. concentrationThe mixture is concentrated to dryness under vacuum
  2. extractionextracted with ethyl ether (2×50 ml)
  3. concentrationThe dried organic phases (Na2SO4) are concentrated to dryness under vacuum
  4. customto give an oil which
  5. customcrystallizes from isopropyl ether (70 ml)
  6. customAfter recrystallization from 2-propanol
  7. customdrying under vacuum at 40° C.

Sources & evidence

ORD record
ord-2283e43de1264f7fb89b66806ad7611c
Source dataset
uspto-grants-1999_11
Patent number
US05977106

Reaction notes

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