Water → HCID 21182312, compound

HRID 1386616Notes

Reaction equation

HRID 1386616 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1)=[O:25])[CH3:22].C([BH3-])#N.[Na+].O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([N:35]3[CH2:34][CH2:33][N:32]([C:29]4[CH:28]=[CH:27][C:26]([C:24]([O:23][CH2:21][CH3:22])=[O:25])=[CH:31][CH:30]=4)[CH2:37][CH2:36]3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydrideHCID 21182250HCID 21182250, compound

Product 1

HCID 21182312HCID 21182312, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-n-Hexyloxyphenyl)-4-piperidone (0.823 g), 1-(4-Ethoxycarbonylphenyl)piperazine (0.7 g), and titanium(IV) isopropoxide (1.11 ml) was stirred at room temperature. After 1 hour, the IR spectrum of the mixture showed no ketone band, and the viscous solution was diluted with absolute ethanol (3 ml). Sodium cyanoborohydride (0.121 g) was added, and the solution was stirred for 3 hours. Water (3 ml) was added with stirring, and the resulting in organic precipitate was filtered and washed with ethanol. The filtrate was extracted with ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure to give Ethyl 4-[4-[1-(4-n-hexyloxyphenyl)piperidin-4-yl]piperazin-1-yl]benzoate (331 mg).

Workup

  1. stirringthe solution was stirred for 3 hours
  2. stirringwith stirring
  3. filtrationthe resulting in organic precipitate was filtered
  4. washwashed with ethanol
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. customfiltrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4581aac8074d4b49a0432420d9853d13
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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