Triethylamine → HCID 59752913, compound

HRID 749997Notes

Reaction equation

HRID 749997 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C>ClCCl.O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][CH2:25][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[CH2:13][O:12][C:11]1[CH:20]=[CH:21][C:8]([O:7][C:6]2[CH:22]=[CH:23][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76934Methyl 3-bromopropanoateHCID 68996119HCID 68996119, compound

Product 1

HCID 59752913HCID 59752913, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-[4-(4-chloro-phenoxy)-phenoxymethyl]-piperidine hydrochloride (218 mg, 0.615 mmol), methyl 3-bromopropionate (128 mg, 0.769 mmol), and triethylamine (124 mg, 1.23 mmol) in dichloromethane (2.5 mL) was heated for 18 h at 30° C. The mixture was diluted with 5 mls of water and extracted with dichloromethane (8 mL). The aqueous layer was re-extracted with ethyl acetate (8 mL). The combined organic layers were dried over anhy. Na2SO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the product (62 mg, 25%): 1H NMR (400 MHz, CDCl3); δ 1.48-1.77 (m, 6H), 2.22-2.36 (m, 1H), 2.52-2.57 (m, 2H), 2.68-2.71 (m, 1H), 2.84-2.97 (m, 2H), 3.09-3.16 (m, 1H), 3.66 (s, 3H), 3.91-3.94 (dd, 1H J1=4.4 Hz, J2=10.0 Hz), 4.02-4.06 (dd, 1H J1=5.2 Hz, J2=10.0 Hz), 6.86-6.96 (m, 5H), 7.23-7.26 (m, 3H)

Workup

  1. extractionextracted with dichloromethane (8 mL)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate (8 mL)
  3. customThe combined organic layers were dried over anhy
  4. customNa2SO4 and the solvent was removed in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-dad3308e9b2543b790e56f457d8aae2f
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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