Ethyl bromoacetate → HCID 54486439, compound

HRID 1769676Notes

Reaction equation

HRID 1769676 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].O.Cl.Cl.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[NH:19][C:20](=[O:28])[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[NH:19][C:20]([CH2:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:26][CH2:27]1)=[O:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 67623008HCID 67623008, compound

Product 1

HCID 54486439HCID 54486439, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl bromoacetate (12.12 g, 0.073 mol) in dry acetonitrile (30 mL) was added dropwise to a mixture of N-(2,6-dimethylphenyl)-1-piperazineacetamide dihydrochloride hydrate (18.0 g, 0.073 mol) and potassium carbonate (18.0 g, 0.13 mol) in dry acetonitrile (200 mL). The mixture was stirred at room temperature for 16 h before it was filtered and evaporated. The residue was partitioned between ethyl acetate and water and the organic phase was separated, washed with brine dried and concentrated. There was isolated 21 g (86%) of the XI compound as a colorless oil which was used without further purification; 1H NMR (300 MHz, DMSO-d6) δ 9.16 (s, 1H), 7.06 (s, 3H), 4.11 (q, J=3.6 Hz, 2H), 3.22 (s, 2H), 3.13 (s, 2H), 2.68 (br s, 8H), 2.14 (s, 6H), 1.19 (t, J=7.0 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 171.65 (0), 169.63 (0), 166.02 (0), 136.72 (0), 136.67 (0), 129.36 (+), 128.09 (+), 63.07 (-), 61.54 (-), 60.24 (-), 54.67 (-), 53.59 (-), 19.7 (+), 15.88 (+); IR (KBr) 3242, 3020, 2988, 2964, 2936, 2914, 2878, 2824, 1744, 1662, 1530, 1478, 1466, 1444, 1428, 1390, 1380, 1306, 1278, 1224, 1198, 1166, 1136, 1042, 1020, 836, 762, 718 cm-1 ; MS (DCI) m/e 334.

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organic phase was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-71f9b3cff2f64cc68e028b06e45d2b3c
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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