Triethylamine → HCID 57440680, compound

HRID 2102340Notes

Reaction equation

HRID 2102340 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[OH:11].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>ClCCl>[OH:11][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH2:9][NH:8][C:20](=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 5866792-Amino-1-(3-methoxyphenyl)ethanol

Product 1

HCID 57440680HCID 57440680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (52 ml, 0.37 mol) was added to the amine from example 1 (31.3 g, 0.19 mol) in dichloromethane (400 ml) and reaction mixture stirred under an atmosphere of nitrogen gas at 0° C. for 10 minutes. Propionyl chloride (16.3 ml, 0.19 mol) was added and after stirring for 30 minutes, the reaction temperature was raised to room temperature for a further 5 hours. The reaction mixture was quenched 1N HCl (aq) (100 ml) and then extracted with dichloromethane (2×50 ml). The organic fractions were combined, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a colourless oil that crystallised on standing to white crystals (28 g, 0.13 mol, 67%). 1H NMR (CDCl3, 400 MHz) δ: 1.18 (t, 3H), 2.22 (q, 2H), 2.51 (bs, 1H), 3.31 (m, 1H), 3.71 (dd, 1H), 3.80 (s, 3H), 4.81 (m, 1H), 5.95 (bs, 1H), 6.80 (d 1H), 6.90 (d 1H), 6.91 (s, 1H), 7.22 (t, 1H). LRMS: m/z 224. Mpt: 77-78° C. Analysis found C, 63.86; H, 7.82; N, 6.28%. C12H17NO30.1H2O requires C, 64.04; H, 7.70; N, 6.22%.

Workup

  1. stirringafter stirring for 30 minutes
  2. temperaturethe reaction temperature was raised to room temperature for a further 5 hours
  3. customThe reaction mixture was quenched 1N HCl (aq) (100 ml)
  4. extractionextracted with dichloromethane (2×50 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9073a864bc64651ad2d71cd6c95af84
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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