Ethanol → HCID 21914400, compound

HRID 1245839Notes

Reaction equation

HRID 1245839 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O)C.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:1])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 7466p-BromoacetophenoneHCID 8082PiperidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21914400HCID 21914400, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

4-Bromoacetophenone (1.95 g), piperidine (0.97 ml) and titanium(IV) isopropoxide (3.64 ml) were stirred under argon at room temperature for 1 h. Ethanol (10 ml) was added, followed by sodium cyanoborohydride (0.41 g) and mixture stirred for 18 h. Water (2 ml) was then added and the mixture stirred for 20 minutes. The resulting inorganic precipitate was filtered off, washed with ethanol (20 ml) and the combined organic phase was concentrated in vacuo, redissolved in toluene and purified by Bondelute® chromotography, eluting with 0–20% ethyl acetate/iso-hexane to give the product as a pale yellow oil (1.07 g).

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. filtrationThe resulting inorganic precipitate was filtered off
  3. washwashed with ethanol (20 ml)
  4. concentrationthe combined organic phase was concentrated in vacuo
  5. dissolutionredissolved in toluene
  6. custompurified by Bondelute® chromotography
  7. washeluting with 0–20% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-216b0b8ea209470ebda97b9986151d62
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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