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Trifluoroacetic acid → N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate

HRID 1349400
Notes
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Reaction equation

HRID 1349400 reaction equation
[C:1]1([C@H:7]([OH:26])[CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18]C(OC(C)(C)C)=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[C:1]1([C@H:7]([OH:26])[CH2:8][NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22986857N-(2-phenyl-2-(S)-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline

Product 1

HCID 22986855N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(2-phenyl-2-(S)-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline (2.5 g, 7.0 mmole) in CH2Cl2 (15 mL) was cooled in an ice bath under stream of nitrogen and TFA (15 mL) was slowly added. The reaction mixture was stirred for 2 h at 0° C. and then concentrated in vacuo. The crude product was dissolved in 20% MeCN/H2O and purified by preparative reversed phase HPLC (5 to 2% MeCN/H2O over 50 min; 254 nm: 20 mL/min.), to give N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate salt 31 as a colorless oil. 1H-NMR (CD)3OD, 299.96 MHz): δ (ppm); 7.45–7.25 (m, 9H), 4.9 (dd, 1H). 3.55–3.45 (m, 2H), 3.21–3.15 (t, 2H), 3.05–2.95 (t, 2H) ESMS (C16H20N2O1): calcd. 256.4, obsd. 257.1 [M+H]+, 280.2 [M+Na]−.

Workup

  1. additionwas slowly added
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude product was dissolved in 20% MeCN/H2O
  4. custompurified by preparative reversed phase HPLC (5 to 2% MeCN/H2O over 50 min; 254 nm: 20 mL/min.)

Sources & evidence

ORD record
ord-1caf8951889e42d4a5c48fab193f66c7
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07211695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes