Triethylamine → HCID 23047428, compound

HRID 2107088Notes

Reaction equation

HRID 2107088 reaction equation
[C:1]1([CH:7](Br)[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH2:24]>C(#N)C.C(OCC)C>[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH:24][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 23047428HCID 23047428, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

A stirred solution of methyl 2-phenyl-2-bromoacetate (53.8 g) in acetonitrile (450 ml) was treated with triethylamine (45.2 ml). The mixture was then cooled in an ice-bath and treated, dropwise during 15 minutes, with a solution of aminoacetaldehyde dimethylacetal (37.8 ml) in acetonitrile (80 ml), keeping the temperature below 45° C. The mixture was stirred at room temperature for 2 hours and then left to stand for 48 hours. The mixture was then diluted with diethyl ether (800 ml) and washed with water (3×250 ml). The ethereal was dried over magnesium sulphate and evaporated, to give methyl 2-(2,2-dimethoxyethylamino)phenylacetate (55.5 g), in the form of a colourless oil [N.M.R. (in CDCl3) 2.10 (1H, b), 2.57-2.79 (2H, m), 3.34 (3H, s), 3.37 (3H, s), 3.68 (3H, s), 4.50 (1H, t, J=6 Hz), 7.35 (5H, m)].

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. customthe temperature below 45° C
  3. waitleft
  4. waitto stand for 48 hours
  5. washwashed with water (3×250 ml)
  6. dry with materialThe ethereal was dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-c9fd5225b8764a6abc554e49a741ddb2
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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