Methanol → HCID 22168547, compound

HRID 1607866Notes

Reaction equation

HRID 1607866 reaction equation
CO.O=[C:4]([CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1.Cl.CN.[C:21]([BH3-])#[N:22].[Na+]>Cl.C(N(CC)CC)C>[CH3:21][NH:22][CH:4]([CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 5003444Sodium cyanoborohydride2×HCID 6364545Methylamine hydrochlorideHCID 13553580Methyl [4-(2-oxopropyl)phenyl]acetate

Product 1

HCID 22168547HCID 22168547, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8471TriethylamineSolvent

Procedure

To 25 mL of methanol 0.59 g of methyl 4-(2-oxopropyl)phenylacetate, prepared above, was added and dissolved. Then with stirring the following were added: 2.0 g methylamine hydrochloride, 0.3 g sodium cyanoborohydride, and 0.3 mL of triethylamine. After approximately 12 hours an additional 0.1 g of sodium cyanoborohydride was added to the mixture. After 3 hours more, the reaction was diluted with 100 mL of 0.1M hydrochloric acid, washed with diethylether, and the resulting aqueous phase was basified to a pH of 12 by addition of 5 mL portions of 1N sodiumhydroxide solution. This was extracted three times with 100 mL portions of diethylether, combined extracts washed with brine and dried. The solvents were removed in vacuo to yield 0.44 g of a light yellow oil.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. additionfollowing were added
  4. washwashed with diethylether
  5. additionthe resulting aqueous phase was basified to a pH of 12 by addition of 5 mL portions of 1N sodiumhydroxide solution
  6. extractionThis was extracted three times with 100 mL portions of diethylether
  7. washcombined extracts washed with brine
  8. customdried
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-e769d335b081444da920905ff357f723
Source dataset
uspto-grants-1989_09
Patent number
US04868132

Reaction notes

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