Trifluoroacetic acid → 105315-95-5

HRID 601025Notes

Reaction equation

HRID 601025 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][C:9]=1[Cl:20])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:20][C:9]1[CH:10]=[C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:12]=[CH:13][C:8]=1[NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59650322HCID 59650322, compound

Product 1

HCID 18549575105315-95-5Yield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of impure (2-chloro-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (2.84 g) in dichloromethane (30 mL) was treated with trifluoroacetic acid (3.5 mL), stirred at room temperature for 24 h and evaporated. The residue was dissolved in ethyl acetate, was washed with 1N NaOH, water, and brine, was dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 35:65 ethyl acetate:hexanes provided 2-chloro-4-morpholin-4-yl-phenylamine (0.77 g, 40% yield) as an off-white solid. 1H-NMR (CDCl3, 500 MHz) 6.92 (br, 1H), 6.77 (br, 2H), 3.89 (m, 6H), 3.05 (m, 4H) ppm; MS (FIA) 213.1 (M+H); HPLC (Method A) 1.975 min.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwas washed with 1N NaOH, water, and brine
  4. dry with materialwas dried (sodium sulfate)
  5. customevaporated
  6. customPurification by flash chromatography (SiO2)
  7. washeluted with 35:65 ethyl acetate

Sources & evidence

ORD record
ord-09385692eb714bcd9b6298309b04ae21
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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