Ethanol → Ethyl 4-(4-((2-bromocyclohex-1-enyl)methyl)piperazin-1-yl)benzoate

HRID 1968602Notes

Reaction equation

HRID 1968602 reaction equation
[Br:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[CH:8]=O.[CH2:10]([O:12][C:13](=[O:26])[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1)[CH3:11].C(O)C.C([BH3-])#N.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[CH2:8][N:23]1[CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([C:13]([O:12][CH2:10][CH3:11])=[O:26])=[CH:19][CH:18]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 702EthanolHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydrideHCID 112639462-Bromocyclohexene-1-carbaldehyde

Product 1

HCID 25139192Ethyl 4-(4-((2-bromocyclohex-1-enyl)methyl)piperazin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 100 mL round bottom flask was charged with 2-bromocyclohex-1-enecarbaldehyde, (prepared as described by Arnold, A. et. al. Collect. Czech. Chem. Commun., 1961, 26, 3059-3073.), (42 mmol), 4-piperazin-1-yl-benzoic acid ethyl ester (42 mmol) and ethanol (50 ml). The mixture was stirred and sodium cyanoborohydride (42 mmol) was added. Acetic acid was used to adjust pH to 5-6. The reaction mixture was stirred under N2 at room temperature overnight. The reaction mixture was filtered and washed with ethanol. The filtered solid was discarded and the combined organic layers were concentrated under vacuum. The mixture was purified by silica gel chromatography eluting with 5-10% ethyl acetate in hexanes to provide the title compound.

Workup

  1. custom(prepared
  2. customet. al. Collect
  3. stirringThe reaction mixture was stirred under N2 at room temperature overnight
  4. filtrationThe reaction mixture was filtered
  5. washwashed with ethanol
  6. concentrationthe combined organic layers were concentrated under vacuum
  7. customThe mixture was purified by silica gel chromatography
  8. washeluting with 5-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4bcf9534ae9b4a1cb5d01fe75323e53d
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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