Trifluoroacetic acid → 4-Methanesulfonyl-6-(piperazin-1-ylmethyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1295560Notes

Reaction equation

HRID 1295560 reaction equation
[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([CH2:15][N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>ClCCl>[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([CH2:15][N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86597571tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate

Product 1

HCID 112091394-Methanesulfonyl-6-(piperazin-1-ylmethyl)-3,4-dihydro-2H-benzo[1,4]oxazineYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate (2.5 g, 6.1 mmol) was dissolved in dichloromethane (50 mL) and treated with trifluoroacetic acid (182 mmol). The resulting mixture was stirred at ambient temperature for 3 h then evaporated to dryness under reduced pressure. The residue was extracted with hot ethanol and the combined extracts evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with 0.880 ammonia/methanol/dichloromethane (1:9:90), gave the title compound (1.2 g, 63%) as an off-white solid.

Workup

  1. customthen evaporated to dryness under reduced pressure
  2. extractionThe residue was extracted with hot ethanol
  3. customthe combined extracts evaporated to dryness under reduced pressure
  4. washChromatography on SiO2, eluting with 0.880 ammonia/methanol/dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-539adfd14804403583c7e978f4ba6976
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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