Trifluoroacetic acid → 4-[4-(2-Benzylamino-ethyl)-phenoxy]-phenylamine

HRID 2197644Notes

Reaction equation

HRID 2197644 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[N:14]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C>ClCCl>[CH2:15]([NH:14][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31]2[CH:32]=[CH:33][C:34]([NH2:37])=[CH:35][CH:36]=2)=[CH:28][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59717849{2-[4-(4-Amino-phenoxy)-phenyl]-ethyl}-benzyl-carbamic acid tert-butyl ester

Product 1

HCID 115006894-[4-(2-Benzylamino-ethyl)-phenoxy]-phenylamineYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (0.24 mL) dropwise to a solution of {2-[4-(4-Amino-phenoxy)-phenyl]-ethyl}-benzyl-carbamic acid tert-butyl ester (100 mg, 0.24 mmol) in dichloromethane (5 mL) at room temperature and stir overnight. Concentrate on a rotary evaporator, dilute with saturated aqueous sodium bicarbonate then extract with dichloromethane (3×50 mL). Dry the dichloromethane extracts over sodium chloride/magnesium sulfate, filter, then concentrate on a rotary evaporator to yield 4-[4-(2-benzylamino-ethyl)-phenoxy]-phenylamine, (38 mg): 1H NMR (CDCl3, 300.00 MHz): 7.42-6.67 (m, 14H), 3.86 (s, 2H), 3.61 (s, 2H), 2.88 (m, 4H); m/z=319.2 (M+1); HPLC=97% (5/95 to 95/5 ACN/(0.1% TFA in water) over 10 minutes, Zorbax SB-Phenyl 4.6 mm×15 cm×5 micron, λ=254 nM.

Workup

  1. concentrationConcentrate on a rotary evaporator
  2. additiondilute with saturated aqueous sodium bicarbonate
  3. extractionthen extract with dichloromethane (3×50 mL)
  4. dry with materialDry the dichloromethane
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator

Sources & evidence

ORD record
ord-60e40321efec48f0b6de48c0dd604624
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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