4-Hydroxybenzaldehyde → HCID 86671378, compound

HRID 1526105Notes

Reaction equation

HRID 1526105 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.O[C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:37]([C:36]1[CH:39]=[CH:40][C:33]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:34][CH:35]=1)=[O:38]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 162178001-Boc-4-(3-hydroxypropyl)piperazine

Product 1

HCID 86671378HCID 86671378, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.61 ml (3.07 mmol) of diisopropyl diazene-1,2-dicarboxylate is added drop by dr op at 0° C. under argon 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 supported triphenylphosphine (3 mmol/g of resin) diluted in 14.5 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature for 20 hours, and then the solid is filtered and rinsed with dichloromethane. The filtrate is concentrated and diluted in sodium hydroxide solution (1 M), the product is extracted several times with ethyl acetate, and then the organic phases are combined, dried on magnesium sulfate and concentrated. The residue is purified by silica gel chromatography (eluent: 4:6 cyclohexane/ethyl acetate 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 colorless oil.

Workup

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

Sources & evidence

ORD record
ord-8b67e208e695418b9ebecb50f7724676
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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