Triethylamine → HCID 69003367, compound

HRID 2103315Notes

Reaction equation

HRID 2103315 reaction equation
[O:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23](=[O:27])[CH2:24][CH2:25]Br.C(N(CC)CC)C>C(Cl)Cl>[CH3:21][O:22][C:23](=[O:27])[CH2:24][CH2:25][N:16]1[CH2:15][CH2:14][CH:13]([O:12][C:11]2[CH:19]=[CH:20][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76934Methyl 3-bromopropanoateHCID 24883357HCID 24883357, compound

Product 1

HCID 69003367HCID 69003367, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-Phenoxy-phenoxy)-piperidine (152 mg, 0.5 mmol) in anhydrous CH2Cl2 (0.5 mL) was added methyl-3-bromopropionate (91 mg, 0.55 mmol) in CH2Cl2 (0.5 mL) and triethylamine (101 mg, 1.0 mmol). The resulting mixture was purged with nitrogen and stirred at rt for 48 h. CH2Cl2 was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with saturated NaHCO3, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography (50% EtOAc/Hexane) to obtain the product (146 mg, 82%): MS; m/z 356.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.56-1.60 (m, 2H), 1.89-1.92 (m, 2H), 2.19-2.49 (m, 2H), 2.46-2.49 (m, 2H), 2.58 (t, 2H, J=6.8Hz), 2.60-2.69 (m, 2H), 3.59 (s, 3H), 4.28-4.30 (m, 1H), 6.91-6.96 (m, 6H), 7.04-7.08 (m, 1H), 7.32-7.36 (m, 2H); HPLC (UV); 94.7%.

Workup

  1. customThe resulting mixture was purged with nitrogen
  2. customCH2Cl2 was removed in vacuo and crude mixture
  3. customEtOAc layer was removed
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel flash chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-2dbb180afab44f83a787ad083220a674
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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