Hydrochloric Acid → 4-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochloride

HRID 352107Notes

Reaction equation

HRID 352107 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[CH2:22]([NH:24][CH2:25][CH2:26][OH:27])[CH3:23].Cl>O1CCCC1.C(OCC)C.ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][N:24]([CH2:22][CH3:23])[CH2:25][CH2:26][OH:27])[CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 80722-(Ethylamino)ethanolHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

Product 1

HCID 698289354-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochlorideYield 65.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A solution of the product from Example 1 step (c) (200 mg) and 2-(ethylamino)ethanol (163 mg, 0.14 ml) in tetrahydrofuran (5 ml) was stirred for 2 days. The solvent was removed in vacuo and the residue dissolved in water and aqueous potassium carbonate and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil. To a solution of this amine in diethyl ether-dichloromethane was added a 1M solution of hydrogen chloride in diethyl ether. The crystals that formed were collected and dried to afford the title compound as a white solid (65 mg). M.p. 141-144° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionaqueous potassium carbonate and extracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil
  8. customThe crystals that formed
  9. customwere collected
  10. customdried

Sources & evidence

ORD record
ord-1479a23a332f49c69d0922977bfafd6d
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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