Triethylamine → HCID 18117857, compound

HRID 1892622Notes

Reaction equation

HRID 1892622 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][NH2:24])=[CH:21][C:16]=2[O:15][CH2:14]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C=O)C>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][NH:24][C:9](=[O:11])[CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[CH:21][C:16]=2[O:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 76257Diethyl cyanophosphonate

Product 1

HCID 18117857HCID 18117857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromophenyl acetic acid 34 (2.000 g, 9.300 mmol) and 2-benzo[1,3]dioxol-5-yl-ethylamine hydrochloride salt 33 (2.063 g, 10.230 mmol) in anhydrous DMF (25 mL) was added triethyl amine (2.823 g, 27.900 mmol) followed by diethyl cyanophosphonate (1.669 g, 10.230 mmol) at 00 C and the reaction mixture was stirred at room temperature overnight, poured into ice-water. The precipitated was filtered, washed with water and air-dried. The crude product was recrystallized using CHCl3-Hexane to get compound 35 as a white sold (3.133 g, 93%). 1H NMR (300 MHz, DMSO-d6) δ 8.06 (t, J=5.1 Hz, 1H, —NH), 7.47 (d, J=8.4 Hz, 2H, ArH), 7.16 (d, J=8.1 Hz, 2H, ArH), 6.79 (d, J=7.8 Hz, 1H, ArH), 6.74 (s, 1H, ArH), 6.60 (d, J=7.8 Hz, 1H, ArH), 5.96 (s, 2H, —CH2), 3.35 (s, 2H, —CH2), 3.32 (q, J=6.9 Hz, 2H, —CH2), 2.60 (t, J=7.2 Hz, 2H, —CH2). MS (ES+) m/z 384 (M+Na)+.

Workup

  1. filtrationThe precipitated was filtered
  2. washwashed with water
  3. customair-dried
  4. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-2e53b5531960461aa438a456049268c1
Source dataset
uspto-grants-2013_08
Patent number
US08507523B2

Reaction notes

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