HCID 20291281, compound → HCID 20291274, compound

HRID 1413946Notes

Reaction equation

HRID 1413946 reaction equation
C([N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([C:29]([Cl:32])([F:31])[F:30])([C:25]([Cl:28])([F:27])[F:26])[OH:24])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>Cl.[Pd]>[ClH:28].[Cl:32][C:29]([F:30])([F:31])[C:23]([C:25]([Cl:28])([F:26])[F:27])([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[NH:14][CH2:15][CH2:16]2)[OH:24]

Participants

4

Reactant 1

HCID 20291281HCID 20291281, compound

Product 1

HCID 20291274HCID 20291274, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

The crude 1-benzhydryl-α,α-bis(chlorodifluoromethyl)-2,3-dihydro-1H-indole-5-methanol is dissolved in a mixture of 200 ml of alcohol and 20 ml of concentrated hydrochloric acid and is hydrogenated at an initial pressure of three atmospheres in the presence of 1.5 g of 10% palladium on charcoal in a Parr shaker apparatus until no further change of pressure is observed. The catalyst is filtered off, and the filtrate is evaporated. The residue is evaporated repeatedly with toluene to remove traces of water. Trituration of the residue with toluene gives crystals, which are filtered off to give 6.2 g of α,α-bis(chlorodifluoromethyl)-2,3-dihydro-1H-indole-5-methanol hydrochloride, m.p. 224°-228° (dec.). For analysis a portion is recrystallized from nitromethane to give crystals, m.p. 228°-229° (dec.). The structure is confirmed by nmr spectroscopy and elemental analysis:

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is evaporated repeatedly with toluene
  4. customto remove traces of water
  5. customTrituration of the residue with toluene gives crystals, which
  6. filtrationare filtered off

Sources & evidence

ORD record
ord-b69dbecc2df54f1189ab4fb967afa596
Source dataset
uspto-grants-1981_02
Patent number
US04251659

Reaction notes

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