Ammonium Hydroxide → HCID 60104785, compound

HRID 1836317Notes

Reaction equation

HRID 1836317 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=O.[NH4+].[OH-]>ClCCl>[CH3:9][C@@H:8]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]([C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[CH3:1])=[N:6][CH2:7]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 26778945HCID 26778945, compound

Product 1

HCID 60104785HCID 60104785, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

(R)-2-Methyl-N-(2-phenyl-propyl)-benzamide (2.1 g; 8.29 mmol) is added all at once to polyphosphoric acid (pre-heated to 140°) and the resulting mixture is stirred at 140° C. for 1 hour. The mixture is poured onto ice, made basic with concentrated NH4OH, and diluted with dichloromethane (100 mL). The phases are separated, and the aqueous phase extracted with dichloromethane (3×70 mL). The combined organics are washed with water (1×50 mL) and brine (1×50 mL), dried over magnesium sulfate, and evaporated in vacuo. The residue is purified by flash chromatography over silica gel (eluting with ether) to give the product as a yellow oil.

Workup

  1. additionThe mixture is poured onto ice
  2. customThe phases are separated
  3. extractionthe aqueous phase extracted with dichloromethane (3×70 mL)
  4. washThe combined organics are washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue is purified by flash chromatography over silica gel (eluting with ether)

Sources & evidence

ORD record
ord-86c25ebaf1094fd5ad437c271a01fa03
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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