Triethylamine → HCID 15034359, compound

HRID 359064Notes

Reaction equation

HRID 359064 reaction equation
[C:1]1([O:7][CH2:8][CH:9]2[O:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:13]([NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:13]([N:20]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH2:10][CH:9]([OH:11])[CH2:8][O:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31217Phenyl glycidyl etherHCID 3042571Phenol, 4-(2-((phenylmethyl)amino)ethyl)-, hydrochloride

Product 1

HCID 15034359HCID 15034359, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of phenylglycidyl ether (8.0 g), N-benzyltyramine hydrochloride (13.0 g) and triethylamine (7.5 ml) in isopropanol (200 ml) was heated to reflux for 3hours. The solvent was evaporated and toluene was added to the residue. Volatile material was evaporated. The residue was purified by chromatography on K60 silica (300 g) using a gradient mixture of methanol in dichloromethane (1 to 2% methanol). Thus was obtained 4-[2-(N-benzyl-N-(2-hydroxy-3-phenoxypropyl)amino)ethyl]phenol (16.5 g) as an oil which slowly crystallised, m.p. 103°-5° C.: NMR: 2.55-2.85[m,6H, CHCH2NHCH2CH2 ]; 3.65-4.05 [m,5H, PhOCH2CHOH +PhCH2 ]; 6.65-7.4[m,14H, aromatic H].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3hours
  3. customThe solvent was evaporated
  4. additiontoluene was added to the residue
  5. customVolatile material was evaporated
  6. customThe residue was purified by chromatography on K60 silica (300 g)
  7. additiona gradient mixture of methanol in dichloromethane (1 to 2% methanol)

Sources & evidence

ORD record
ord-b8cc23800e474d20a7d87ffc089cbf50
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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