Water → HCID 19767280, compound

HRID 1590533Notes

Reaction equation

HRID 1590533 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1)([O-:22])=[O:21].O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CN1C(=O)N(C)CCC1>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]1[CH2:33][CH2:34][N:29]([C:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7416311-Bromo-1-undecanolHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 19767280HCID 19767280, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
85 °C

Procedure

10 g of 11-bromoundecan-1-ol, 4 g of dry potassium carbonate powder, 8.27 g of 4-nitrophenylpiperazine and 2 drops of the conventional and known phase transfer catalyst Aliquat® 336 in 50 ml of dimethylpropyleneurea were heated at 85° C. for 6 hours and then left to stand for 2 days. The reaction mixture was then poured into 500 ml of water. The precipitated crude product was filtered off under suction (first fraction). The water phase was extracted a further three times with 50 ml of toluene in each case and four times with 50 ml of ethyl acetate in each case. The combined extracts were evaporated down and the remaining crude product fraction (second fraction) was combined with the first fraction, after which the combined crude product fractions were recrystallized from a mixture of ethanol and water in a volume ratio of 2:1. The recrystallized product was dried under reduced pressure, after which 7.8 g of N-(11-hydroxyundecyl)-N'-(4-nitrophenyl)-piperazine resulted. The product had the following physical properties: melting point 118° C., IR spectrum (KBr pellet): bands at 3,550, 2,900, 2,850, 1,595, 1,575, 1,470, 1,333, 1,255, 1,250, 1,115, 820 and 750 cm-1 ; elemental analysis: calculated 66.8% C, 9.34% H, 11.13% N and 12.7% O; found: 66.8% C, 9.4% H, 11.1% N and 12.7% O.

Workup

  1. waitleft
  2. customThe precipitated crude product
  3. filtrationwas filtered off under suction (first fraction)
  4. extractionThe water phase was extracted a further three times with 50 ml of toluene in each case and four times with 50 ml of ethyl acetate in each case
  5. customThe combined extracts were evaporated down
  6. customwere recrystallized from a mixture of ethanol and water in a volume ratio of 2:1
  7. customThe recrystallized product was dried under reduced pressure

Sources & evidence

ORD record
ord-d70b31f3710449968dc95eec4d01ed7f
Source dataset
uspto-grants-1993_04
Patent number
US05204178

Reaction notes

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