Triethylamine → 2-(4-Fluoro-phenoxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-nicotinamide

HRID 844083Notes

Reaction equation

HRID 844083 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:11])[CH3:10])[CH2:5][CH:4]=1.Cl.C(N(CC)CCCl)C.[F:22][C:23]1[CH:38]=[CH:37][C:26]([O:27][C:28]2[N:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30](O)=[O:31])=[CH:25][CH:24]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:27][C:28]2[N:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([NH:1][CH2:2][C:3]2[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:10])[CH3:11])[CH2:5][CH:4]=2)=[O:31])=[CH:37][CH:38]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 6051232-(4-Fluorophenoxy)nicotinic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 226122252-(4-Aminomethyl-cyclohex-3-enyl)-propan-2-ol

Product 1

HCID 226122062-(4-Fluoro-phenoxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-nicotinamideYield 9.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-Aminomethyl-cyclohex-3-enyl)-propan-2-ol (0.360 grams, 2.127 mmole), 2-diethylaminoethyl chloride hydrochloride (0.530 grams, 2.765 mmole), 2-(4-Fluoro-phenoxy)-nicotinic acid (0.645 grams, 2.765 mmole), 1-hydroxybenzotriazole hydrate (0.374 grams, 2.765 mmole) and triethyl amine (0.430 grams, 4.254 mmole) in methylene chloride (40 ml) was added and stirred over night. The mixture was concentrated and partitioned between ethyl acetate and 1 N HCl. The organic extracts were washed with saturated sodium hydrogencarbonate and brine, dried over MgSO4, filtered and concentrated to give an oil which was purified by chromatography on silica eluting with 50% ethyl acetate/hexane to 100% ethyl acetate to give a yellow oil (0.080 g); M.W. 384.455; MS 385 (M++1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and 1 N HCl
  3. washThe organic extracts were washed with saturated sodium hydrogencarbonate and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas purified by chromatography on silica eluting with 50% ethyl acetate/hexane to 100% ethyl acetate

Sources & evidence

ORD record
ord-fb963c79262b485eb439c77b6ad35565
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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