Phenothiazine → HCID 22599057, compound

HRID 1759673Notes

Reaction equation

HRID 1759673 reaction equation
C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1CCN2C(=NCCC2)CC1.[CH2:35]([O:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)=[CH:48][CH:47]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44]>CN(C)C=O>[CH2:35]([O:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:57][CH2:56][N:55]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:54][CH2:53]2)=[CH:48][CH:47]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44]

Participants

6

Reactant 4

HCID 7108PhenothiazineHCID 81401-BromooctaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22599025HCID 22599025, compound

Product 1

HCID 22599057HCID 22599057, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A total of 0.2 g of a polymerization inhibitor (phenothiazine) was dissolved in N,N-dimethylformamide. To the resulting solution were added and dissolved 0.62 g (0.0032 mol) of octyl bromide, 2.5 g (0.016 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1 g (0.0032 mol) of the above-prepared 1-[4-(9-decenyloxy)phenyl]piperazine, followed by a reaction at 60° C. in an atmosphere of nitrogen gas for 48 hours with stirring. After completion of the reaction, the solution was poured into ice water, extracted with two portions of 300 mL of diethyl ether, washed with 300 mL of distilled water and dehydrated over anhydrous sodium sulfate overnight. After filtration, the solution was diluted with hexane and separated into soluble matters and insoluble matter. The hexane-soluble matter was then recrystallized from ether and hexane (1:3) and thereby yielded the target compound, 1-[4-(9-decenyloxy)phenyl]-4-octylpiperazine.

Workup

  1. additionTo the resulting solution were added
  2. customfollowed by a reaction at 60° C. in an atmosphere of nitrogen gas for 48 hours
  3. customAfter completion of the reaction
  4. extractionextracted with two portions of 300 mL of diethyl ether
  5. washwashed with 300 mL of distilled water
  6. customdehydrated over anhydrous sodium sulfate overnight
  7. filtrationAfter filtration
  8. additionthe solution was diluted with hexane
  9. customseparated into soluble matters and insoluble matter
  10. customThe hexane-soluble matter was then recrystallized from ether and hexane (1:3)

Sources & evidence

ORD record
ord-cc9d001da0b345eeb893692fa1a28cef
Source dataset
uspto-grants-2005_01
Patent number
US06838129B2

Reaction notes

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