3-Hydroxybenzaldehyde → HCID 21846101, compound

HRID 619197Notes

Reaction equation

HRID 619197 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][N:11]1[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 21846101HCID 21846101, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-hydroxybenzaldehyde (8 g, 65 mmol), 1-methyl-4-piperidinol (7.5 g, 65 mmol), triphenylphosphine (13.1 g, 65 mmol) and THF (100 ml) was added diethylazodicarboxylate (11.4 g, 65 mmol) in THF (20 ml) over a 35 minute period. The reaction mixture was stirred in an ice bath for 3 hours, then at room temperature for 5 days. The reaction mixture was concentrated in vacuo, and partitioned between CHCl3 (300 ml) and 3N HCl (300 ml). The aqueous layer was concentrated in vacuo, the residue was treated with 10% K2CO3 and extracted with CHCl3 (2×100 ml). The solvent was removed in vacuo to afford 7.4 g of crude 3-(1-methyl-4-piperidinyloxy)benzaldehyde.

Workup

  1. waitat room temperature for 5 days
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between CHCl3 (300 ml) and 3N HCl (300 ml)
  4. concentrationThe aqueous layer was concentrated in vacuo
  5. additionthe residue was treated with 10% K2CO3
  6. extractionextracted with CHCl3 (2×100 ml)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c28e4d1a7276414ea70528940fac7412
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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