Trifluoroacetic acid → Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

HRID 864845Notes

Reaction equation

HRID 864845 reaction equation
FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][C:11]([N:14]([C:22]2[CH:38]=[CH:37][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:24][CH:23]=2)C(OC(C)(C)C)=O)=[CH:10][CH:9]=1>ClCCl>[N:8]1[CH:13]=[CH:12][C:11]([NH:14][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:37][CH:38]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18918347ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

Product 1

HCID 18918592Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a stirred solution of ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate (260 mg) dissolved in dichloromethane (3 ml). After 18 hours the solvents were removed in vacuo and the residual gum dissolved in dichloromethane. This solution was treated with a saturated solution of sodium hydrogen carbonate. The organic phase was washed with water, dried and evaporated. Trituration of the residue with hexane gave the title compound, 120 mg, as a white solid: m.p. 104°-106° C.; NMR (CDCl3) δ8.22 (2H, d), 7.12 (2H, d), 6.90 (2H, d), 6.64 (.2H, dd), 5.82 (1H, s), 4.13 (2H, q), 3.97 (2H, t), 2.34 (2H, t), 1.80 (2H, m), 1.70 (2H, m), 1.53 (2H, m), 1.27 (3H, t); m/e 329 (M+H)+ ; calculated for C19H24N2O3.0.25H2O: C, 68.6; H, 7.4; N, 8.4. found: C, 68.8; H, 7.3; N, 8.2%.

Workup

  1. customAfter 18 hours the solvents were removed in vacuo
  2. dissolutionthe residual gum dissolved in dichloromethane
  3. additionThis solution was treated with a saturated solution of sodium hydrogen carbonate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-fa616cee9d3745b9839d3048beee2077
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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