Triethylamine → HCID 69070654, compound

HRID 1822028Notes

Reaction equation

HRID 1822028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[CH2:10][CH:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:30][C:31]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:38]([F:40])=[CH:39][C:31]=3[Cl:30])[CH:16]=2)[CH2:10][CH:9]1[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 69067004HCID 69067004, compound

Product 1

HCID 69070654HCID 69070654, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 4-(3-amino-phenoxy)-2-methyl-piperidine-1-carboxylic acid tert-butyl ester cis isomer 1 (preparation 35, 0.40 g, 1.31 mmol), 1,4-dioxane (20 mL), triethylamine (0.22 mL, 1.57 mmol) and 2-chloro-4-fluoro-benzoyl chloride (0.30 g, 1.57 mmol) with stirring. After 4 hr., partition between 4:1 hexane:ethyl acetate (100 mL) and 0.5M aqueous sodium hydroxide solution (100 mL). Separate the organic layer, dry over sodium sulfate, filter and concentrate to obtain of the title compound (0.60 g, 100%): 1H NMR (CDCl3): 7.9 (bs, 1H), 7.8 (dd, 1H), 7.45 (m, 1H), 7.25 (m, 1H), 7.2 (dd, 1H), 7.1 (m, 1H), 7.0 (dd, 1H), 6.7 (dd, 1H), 4.7 (m, 1H), 4.35 (m, 1H), 3.9 (m, 1H), 3.25 (m, 1H), 2.0 (m, 2H), 1.9 (m, 1H), 1.7 (m, 1H), 1.45 (s, 9H), 1.3 (d, 3H).

Workup

  1. custom, partition between 4:1 hexane
  2. customSeparate the organic layer
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b5c2c6c0267640db8f12e2f044ee115c
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

Loading…