Triethylamine → HCID 68998458, compound

HRID 2103317Notes

Reaction equation

HRID 2103317 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.[CH2:28](N(CC)CC)C>C(Cl)Cl>[CH3:21][O:22][C:23](=[O:27])[CH2:24][CH2:25][CH2:28][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 68998458HCID 68998458, compoundYield 68%

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 (99 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 if for 48 h. CH2Cl2 was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with brine, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography (40-70% EtOAc/Hexane) to obtain the product as yellow oil (125 mg, 68%): 1H NMR (400 MHz, DMSO-d6); δ 1.54-1.69 (m, 4H), 1.89-1.92 (m, 2H), 2.14-2.18 (m, 2H), 2.26-2.33 (m, 4H), 2.64-2.67 (m, 2H), 3.58 (s, 3H), 4.27-4.31 (m, 1H), 6.91-6.96 (m, 6H), 7.04-7.08 (m, 1H), 7.32-7.36 (m, 2H).

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 brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel flash chromatography (40-70% EtOAc/Hexane)

Sources & evidence

ORD record
ord-e549668bbc9444d2a07015e8d8c5527b
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

Loading…