Benzylamine → HCID 66916802, compound

HRID 572701Notes

Reaction equation

HRID 572701 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.O.O.O.C([O-])(=O)C.[Na+].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+].[OH-].[Na+].CC(O)C.[ClH:37]>O.C(OCC)(=O)C.CO.C(O)(=O)C>[ClH:37].[CH2:21]([NH:28][C@H:10]([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

11

Reactant 6

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 4311764Sodium borohydrideHCID 21912024Isopropanol hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 66916802HCID 66916802, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Methoxy phenyl acetone (50 kg, 0.305 M), sodium acetate trihydrate (62 kg, 0.455 M) were charged in to the reactor containing acetic acid (170 kg,) and methanol (160 lit). The reaction mass was chilled to 0-5° C. Benzylamine (36 kg, 0.336 M) was added slowly into the reactor maintaining temperature between 0-5° C. After stirring for two hours at 0-5° C., the reaction mass was treated with sodium borohydride (25 kg, 0.657 M) maintaining temperature below 10° C. and was stirred further for 2 hours. The reaction mass was diluted with water (500 lit) and treated with a solution of sodium hydroxide (70 kg sodium hydroxide in 150 lit water) below 30° C. The reaction mass was extracted with methylene chloride twice (200 lit), washed with water and concentrated under reduced pressure. The residue obtained was dissolved in ethyl acetate (200 lit), cooled to 10-15° C. and the pH of reaction mass was adjusted to 1-2 with IPA+HCl. The solids were isolated by filtration, dried to yield title compound as hydrochloride salt. (50 Kg, 56.5%)

Workup

  1. temperaturemaintaining temperature between 0-5° C
  2. temperaturemaintaining temperature below 10° C.
  3. stirringwas stirred further for 2 hours
  4. extractionThe reaction mass was extracted with methylene chloride twice (200 lit)
  5. washwashed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. temperaturecooled to 10-15° C.
  9. customthe pH of reaction mass
  10. customThe solids were isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-1562b07adaf744649bab6baab6c3f6de
Source dataset
uspto-grants-2015_05
Patent number
US09029421B2

Reaction notes

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