4-Hydroxybenzaldehyde → HCID 86671378, compound

HRID 336828Notes

Reaction equation

HRID 336828 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.O[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:23]([C:22]1[CH:25]=[CH:26][C:19]([O:1][CH2:2][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[CH:20][CH:21]=1)=[O:24]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 162178001-Boc-4-(3-hydroxypropyl)piperazine

Product 1

HCID 86671378HCID 86671378, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.5 g (2.05 mmol) of tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate, 0.3 g (2.46 mmol) of 4-hydroxybenzaldehyde and 1 g (3.07 mmol) of resin-supported triphenyl-phosphine (3 mmol/g of resin) diluted in 14.5 ml of anhydrous tetrahydrofuran, is added dropwise at 0° C. under argon 0.614 ml (3.07 mmol) of diisopropyldiazene-1,2-dicarboxylate. The reaction mixture is stirred at room temperature for 20 h. The solid is filtered then rinsed in dichloromethane. The filtrate is concentrated and diluted in a sodium hydroxide solution (1M) and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 4:6 to 100% ethyl acetate) to yield 0.58 g of tert-butyl 4-(3-(4-formylphenoxy)propyl)piperazine-1-carboxylate in the form of a colourless oil.

Workup

  1. filtrationThe solid is filtered
  2. washthen rinsed in dichloromethane
  3. concentrationThe filtrate is concentrated
  4. additiondiluted in a sodium hydroxide solution (1M)
  5. extractionthe product is extracted several times with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 4:6 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-e604bae373f4433b95b4ee70a0f7029a
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

Loading…