Hydrochloric Acid → Methyl alpha-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate hydrochloride

HRID 5609Notes

Reaction equation

HRID 5609 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:7][CH:8]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1)[C:9]([O:11][CH3:12])=[O:10].[ClH:34]>CCOCC>[ClH:34].[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:7][CH:8]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54131001Methyl alpha-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate

Product 1

HCID 67883724Methyl alpha-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A magnetically stirred solution of methyl α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate (4.07 g, 9.0 mmol) in 65 mL of ether cooled at 0°-5° C. was treated dropwise over a four-minute period with a stock solution of hydrogen chloride in ether (3.8 mL, 11.71 mmol, 1.3 eq, 3.1 mmol per mL). The cooling bath was removed after addition was completed and the mixture stirred at room temperature overnight. The precipitated white solid was collected, washed with ether-hexane (1:1) and recrystallized from acetone-ethyl acetate-ether solvent mixture to yield 4.18 g (95%) of the title compound.

Workup

  1. customThe cooling bath was removed
  2. additionafter addition
  3. customThe precipitated white solid was collected
  4. washwashed with ether-hexane (1:1)
  5. customrecrystallized from acetone-ethyl acetate-ether solvent mixture

Sources & evidence

ORD record
ord-60b3074aefe344eab4ea2ade849112af
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Reaction notes

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