Ethylamine → N,N-Diisopropyl-3-(5-ethylaminomethyl-2-hydroxyphenyl)-3-phenylpropanamine

HRID 428329Notes

Reaction equation

HRID 428329 reaction equation
[CH:1]([N:4]([CH:23]([CH3:25])[CH3:24])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([CH:20]=O)[CH:17]=[CH:16][C:15]=1[OH:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[CH2:26]([NH2:28])[CH3:27].C([BH3-])#N.[Na+]>CO>[CH:23]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH2:20][NH:28][CH2:26][CH3:27])[CH:17]=[CH:16][C:15]=1[OH:22])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 53380832(R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine

Product 1

HCID 18357409N,N-Diisopropyl-3-(5-ethylaminomethyl-2-hydroxyphenyl)-3-phenylpropanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(R)-N,N-Diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine (prepared in Example 7.1) (1.23 g, 3.62 mmol) was dissolved in methanol (20 mL). Ethylamine [3.62 mL, 21.7 mmol (6M hydrochloric acid in methanol)] and sodium cyanoborohydride (0.14 g, 2.17 mmol) were added. The mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1). The product was dissolved in diethyl ether and hydrogen chloride in diethyl ether was added. The resulting oil was stirred in diethyl ether over night to give crystals. Yield 0.70 g (44%); mp. 140-142° C.; [α]D−5.0° (c=0.5, methanol); 1H NMR (CD3OD) δ1.30 (m, 15H), 2.59 (m, 2H), 3.05 (m, 4H), 3.70 (m, 2H), 4.07 (s, 2H), 4.42 (t, 1H), 6.85 (d, 1H), 7.20 (m, 2H), 7.30 (t, 2H), 7.41 (d, 2H), 7.50 (s, 1H) Anal. (C24H36N2O*2.0 HCl*0.5H2O) C,H,N.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1)
  3. dissolutionThe product was dissolved in diethyl ether
  4. additionhydrogen chloride in diethyl ether was added
  5. stirringThe resulting oil was stirred in diethyl ether over night
  6. customto give crystals

Sources & evidence

ORD record
ord-5be98d07de0146a09fac8eb164d3e77b
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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