Sodium borohydride → 3-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

HRID 887064Notes

Reaction equation

HRID 887064 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17](OCC)=[O:18])[CH2:11][CH2:10]1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12234156Ethyl 3-[4-(2-methoxyphenyl)piperazino]propanoate

Product 1

HCID 4109013-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(4-(methoxyphenyl)piperazin-1-yl)propanoate (17a) (0.0048 mol) and sodium borohydride (5.4 g, 0.14 mol) in 100 mL anhydrous ethanol was refluxed for overnight (12 h). The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was concentrated on rotavapor. The residue was diluted with DCM, washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL), dried over sodium sulphate (Na2SO4) and evaporated under reduced pressure to give 3-(4-(methoxyphenyl)piperazin-1-yl)propan-1-ol (21a) which was purified by silica gel column chromatography using 0-5% gradient of ethyl acetate and methanol. White solid, 0.6 g (50%). 1H NMR (400 MHz, CDCl3): δ 1.75 (quintet, J=5.2 Hz, 2H); 2.69 (t, J=6.0 Hz, 2H), 2.74 (broad s, 4H); 3.08 (broad s, 4H); 3.82 (t, J=5.2 Hz, 2H); 3.85 (s, 3H); 5.35 (broad s, 1H); 6.84-6.86 (m, 1H); 6.90-6.93 (m, 2H); 6.97-7.02 (m, 1H). MS (ESI): m/z=251.40 (M+H+).

Workup

  1. temperaturewas refluxed for overnight (12 h)
  2. concentrationThe reaction mixture was concentrated on rotavapor
  3. additionThe residue was diluted with DCM
  4. washwashed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL)
  5. dry with materialdried over sodium sulphate (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-800566ac5c2947ba8690d68bb1b32be4
Source dataset
uspto-grants-2012_08
Patent number
US08247420B2

Reaction notes

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