Methanol → HCID 20087955, compound

HRID 2255137Notes

Reaction equation

HRID 2255137 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[CH:11]([CH2:12][N:13]3[CH2:18][CH2:17][N:16](CC4C=CC=CC=4)[CH2:15][CH2:14]3)[O:10][CH2:9][CH2:8][C:7]=2[CH:26]=1.CO>[Pd].O>[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[CH:11]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:10][CH2:9][CH2:8][C:7]=2[CH:26]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 20087940HCID 20087940, compound

Product 1

HCID 20087955HCID 20087955, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 53 g of 1-[(3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)methyl]-4-(phenylmethyl)piperazine, 150 ml of methanol, 150 ml of water and 5 g of 5% Pd on activated charcoal was acidified with 36% hydrochloric acid and hydrogenated at 50 psi until absorption of hydrogen was finished. The catalyst was filtered and the solvent evaporated, after which the residue was basified with sodium hydroxide and extracted with dichloromethane. The dichloromethane phase was washed, dried and evaporated and the product precipitated under diisopropyl ether to obtain 1-[(3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)methyl]piperazine.

Workup

  1. customwas acidified with 36% hydrochloric acid and hydrogenated at 50 psi until absorption of hydrogen
  2. filtrationThe catalyst was filtered
  3. customthe solvent evaporated
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane phase was washed
  6. customdried
  7. customevaporated
  8. customthe product precipitated under diisopropyl ether

Sources & evidence

ORD record
ord-58ffd5f0f7974f228e7835ce4f85b444
Source dataset
uspto-grants-1993_08
Patent number
US05238939

Reaction notes

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