Trifluoroacetic acid → HCID 59717864, compound

HRID 601592Notes

Reaction equation

HRID 601592 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)(C)(C)C>ClCCl>[NH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59717857HCID 59717857, compound

Product 1

HCID 59717864HCID 59717864, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (10 mL) dropwise to a solution of {2-[4-(4-acetylamino-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3.7 g, 10 mmol) in dichloromethane (50 mL) at 0° C. Warm to room temperature and stir overnight. Concentrate on a rotary evaporator, dissolve residue in methanol then apply to a strong cation exchange column (Varian, 0.79 meq/g), and wash with methanol. Elute the product with 2M ammonia in methanol then concentrate on a rotary evaporator to yield N-{4-[4-(2-amino-ethyl)-phenoxy]-phenyl}-acetamide (2.3 g): 1H NMR (DMSO-D6, 300.00 MHz): 9.97 (s, 1H), 7.58 (d, 2H, J=8.8 Hz), 7.19 (d, 2H, J=7.9 Hz), 6.92 (dd, 4H, J=21.3, 8.1 Hz), 3.60-3.05 (m, 3H), 2.73-2.55 (m, 3H), 2.04 (s, 3H).

Workup

  1. concentrationConcentrate on a rotary evaporator
  2. dissolutiondissolve residue in methanol
  3. washapply to a strong cation exchange column (Varian, 0.79 meq/g), and wash with methanol
  4. washElute the product with 2M ammonia in methanol
  5. concentrationthen concentrate on a rotary evaporator

Sources & evidence

ORD record
ord-bd1d17906db14eb5a2e61c85c2eed258
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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