Acetic Anhydride → HCID 178474959, compound

HRID 725835Notes

Reaction equation

HRID 725835 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].[H][H].[C:17](OC(=O)C)(=[O:19])[CH3:18]>[Ni].O>[C:17]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:6][CH2:7]1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 754513-(4-Aminophenyl)propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 178474959HCID 178474959, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 397 g of 3-(4-amino-phenyl)propionic acid, 125 g of NaOH and 160 g of Raney nickel in 5.71 of water is hydrogenated at 170° C. and 100 bar until no further hydrogen is taken up (30 hours). After filtration and washing the residue with water, 6.31 of a colourless solution are obtained as the filtrate, which is combined with a solution of 129 g of NaOH in 400 ml of water, after which 454 ml of acetic anhydride are added dropwise thereto within 35 minutes. After 5 hours the precipitate is filtered off, the filtrate is adjusted to pH 4 by the addition of concentrated hydrochloric acid and stirred for 3 hours at 0° C. It is then suction filtered, washed with 250 ml of ice water and dried at 70° C. In this way, 216 g of 3-(trans-4-acetylaminocyclohexyl)propionic acid are obtained.

Workup

  1. customis hydrogenated at 170° C.
  2. custom(30 hours)
  3. filtrationAfter filtration
  4. washwashing the residue with water, 6.31 of a colourless solution
  5. customare obtained as the filtrate, which
  6. filtrationAfter 5 hours the precipitate is filtered off
  7. additionthe filtrate is adjusted to pH 4 by the addition of concentrated hydrochloric acid
  8. filtrationsuction filtered
  9. washwashed with 250 ml of ice water
  10. customdried at 70° C

Sources & evidence

ORD record
ord-741f1f6dcd12400f872e8baab9a0a062
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

Loading…