Sulfuric Acid → HCID 20638932, compound

HRID 565709Notes

Reaction equation

HRID 565709 reaction equation
[NH2:1][C:2]1[C:3]([CH3:35])=[C:4]([CH3:34])[C:5]2[O:9][C@:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:32]=1[CH3:33].[S:36](=[O:40])(=[O:39])([OH:38])[OH:37]>CO.C(OCC)(=O)C>[S:36]([OH:40])([OH:39])(=[O:38])=[O:37].[NH2:1][C:2]1[C:3]([CH3:35])=[C:4]([CH3:34])[C:5]2[O:9][C@:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:32]=1[CH3:33]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 20638933HCID 20638933, compound

Product 1

HCID 20638932HCID 20638932, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenyl-methyl)-4-piperidinamine (3.5 g) in a mixture of methanol (15 mL) and ethyl acetate (5 mL) was added 2N-sulfuric acid (7.5 mL) and the mixture was concentrated under reduced pressure. To the residue was added methanol (15 mL) and the mixture was stood for 18 hours. The solid formed were collected, dried and recrystallized from methanol-water to provide 3.5 g of the title compound. Yield 75%.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue was added methanol (15 mL)
  3. customThe solid formed
  4. customwere collected
  5. customdried
  6. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-560ebc18e6d14ca2a676b1e162501e48
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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