Acetic Acid → 1-amino-2,3-dihydro-7-hydroxy-4-methyl-6-piperidinylacetylaminomethyl-1H-indene dihydrochloride

HRID 345138

Reaction equation

HRID 345138 reaction equation
[Cl-:1].[OH:2][C:3]1[C:4]([CH2:15][NH:16][C:17]([CH2:19][N+:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[CH:5][C:6]([CH3:14])=[C:7]2[C:11]=1[C:10](=[N:12]O)[CH2:9][CH2:8]2.C(O)(=O)C.[H][H].Cl>CO.[Pt]=O.C(O)C.C(OCC)C>[ClH:1].[ClH:1].[NH2:12][CH:10]1[C:11]2[C:7](=[C:6]([CH3:14])[CH:5]=[C:4]([CH2:15][NH:16][C:17](=[O:18])[CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:3]=2[OH:2])[CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 136364579(2,3-dihydro-7-hydroxy-1-hydroxyimino-4-methyl-1H-indene-6-yl)methylaminocarbonylmethylpyridinium chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 678827031-amino-2,3-dihydro-7-hydroxy-4-methyl-6-piperidinylacetylaminomethyl-1H-indene dihydrochloride

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×HCID 21585056Diethyl ether ethanolSolvent

Procedure

10 Grams of (2,3-dihydro-7-hydroxy-1-hydroxyimino-4-methyl-1H-indene-6-yl)methylaminocarbonylmethylpyridinium chloride, 200 ml of acetic acid and 1.0 g of platinum oxide were subjected to catalytic hydrogenation under 3 atmospheric hydrogen gas pressure at room temperature for 8 hours. After the hydrogenation was completed, the catalyst was removed by filtration, and the filtrate was concentrated to dryness under a reduced pressure. The residue thus obtained was dissolved in 100 ml of methanol and under ice-cooled condition, a methanol solution saturated with hydrogen chloride gas was added thereto so as to adjust the pH of the solution to about pH 1, then the said solution was concentrated to dryness under a reduced pressure. The residue thus obtained was recrystallzed from ethanol-diethyl ether to obtain 4.8 g of 1-amino-2,3-dihydro-7-hydroxy-4-methyl-6-piperidinylacetylaminomethyl-1H-indene dihydrochloride. Colorless powdery crystals. Melting point: 146° C. (decomposed).

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness under a reduced pressure
  3. customThe residue thus obtained
  4. temperaturecooled condition
  5. concentrationthe said solution was concentrated to dryness under a reduced pressure
  6. customThe residue thus obtained

Sources & evidence

ORD record
ord-4577fa8445fd490d838108830b59e380
Source dataset
uspto-grants-1991_10
Patent number
US05055474

Linked notes

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