4-(Trifluoromethoxy)benzylamine → HCID 10385941, compound

HRID 1292202Notes

Reaction equation

HRID 1292202 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)(=O)=O)=CC=1.[F:27][C:28]([F:39])([F:38])[O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CS(C)=O.C(OCC)(=O)C.CCCCCC>[F:27][C:28]([F:38])([F:39])[O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][CH2:11][CH:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 15381104(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one

Product 1

HCID 10385941HCID 10385941, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
90 °C

Procedure

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one (1.0 g, 2.7 mmole) and 4-trifluoromethoxybenzylamine (2.0 g, 11 mmole) were combined in 30 ml of dry DMSO and heated to 90° C. for 4 hours under an argon atmosphere. After cooling to room temperature, the mixture was diluted with 400 ml of 1:1 ethyl acetate/hexane and washed with 400 ml of saturated sodium bicarbonate solution, with two 250 ml portions of water and with saturated brine. The mixture was dried over sodium sulfate, filtered and concentrated in vacuum to yield an oil, which was column chromatographed on silica gel using 1% methanol/CHCl3 as eluant. The free base of the title compound (0.49 g) thus obtained was crystallized from ethanol with the addition of one equivalent of fumaric acid to give 0.29 g of the (S) enantiomer of the title compound as a white solid fumarate, m.p. 201°-202° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 400 ml of saturated sodium bicarbonate solution, with two 250 ml portions of water and with saturated brine
  3. dry with materialThe mixture was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customto yield an oil, which
  7. customchromatographed on silica gel using 1% methanol/CHCl3 as eluant

Sources & evidence

ORD record
ord-b2d17d7c080740bca88afe4bcf5c9d8d
Source dataset
uspto-grants-1998_05
Patent number
US05756532

Reaction notes

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