Trifluoroacetic acid → 1-(2-Methoxyphenyl)-1,4-diazepane

HRID 1250154Notes

Reaction equation

HRID 1250154 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 66631820Tert-butyl 4-(2-methoxyphenyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 149548221-(2-Methoxyphenyl)-1,4-diazepaneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To 2.03 g (6.62 mmol) of 4-(2-methoxy-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester in 30 mL CH2Cl2 at 23° C. was added 5 mL trifluoroacetic acid. After stirring at 23° C. for 30 min, 4 additional mL of trifluoroacetic acid were added. After a total of 1 h, the reaction solution was poured into 200 mL of saturated aqueous NaHCO3 and extracted with 3×100 mL of EtOAc. The combined organics were washed with 1×200 mL H2O, 1×200 mL brine, dried over Na2SO4, filtered and evaporated to give 1.01 g (4.90 mmol, a 74% yield) of the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3): δ1.99 (pent, J=4.5 Hz, 2H), 2.82 (brs, 1H), 3.06 (t, J=4.4 Hz, 2H), 3.08-3.13 (m, 2H), 3.29-3.36 (m, 4H), 3.84 (s, 3H), 6.83-6.96 (m, 4H); IR (KBr, cm−1): 3335w;, MS (ES) m/z (relative intensity): 207 (M++H, 100).

Workup

  1. extractionextracted with 3×100 mL of EtOAc
  2. washThe combined organics were washed with 1×200 mL H2O, 1×200 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give 1.01 g (4.90 mmol

Sources & evidence

ORD record
ord-c0622e0ac1794c3c95543ceb923671ed
Source dataset
uspto-grants-2002_01
Patent number
US06337326B1

Reaction notes

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