Triethylamine → HCID 69000411, compound

HRID 1909689Notes

Reaction equation

HRID 1909689 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.[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>ClCCl.O>[C:24]([O:28][C:29](=[O:32])[CH2:30][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)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 68996119HCID 68996119, compound

Product 1

HCID 69000411HCID 69000411, compoundYield 47.1%

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), t-butylbromoacetate (150 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 title product (125 mg, 47%).

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-4168bdfb1416488e8189c95392279567
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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