Hydrochloric Acid → HCID 18924114, compound

HRID 1290547Notes

Reaction equation

HRID 1290547 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=1.[OH-].[Na+].Cl>CO>[CH3:28][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18918492HCID 18918492, compound

Product 1

HCID 18924114HCID 18924114, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-[4-[3-(4-dimethylaminopyrid-3-yl)propyloxy]phenoxy]butyrate (160 mg) in methanol (10 ml) was added sodium hydroxide solution (2.0 ml of 1.0M) and the solution left until all starting ester had disappeared (Tlc). The reaction mixture was neutralised with hydrochloric acid (2.0 ml) of 1.0M) and evaporated in vacuo. A small amount (5 ml) of water was added and the resulting solution extracted with dichloromethane (3×15 ml). The organic extracts were combined, dried (PS paper) and evaporated to yield the title compound as colourless prisms, (90 mg) m.p. 106°-108° C. (from ethyl acetate); NMR (d6DMSO) δ 1.8-2.1(2H,q;2H,q); 2.4(2H,t); 2.8(2H,t;6H,s); 3.9(2H,t;2H,t); 6.8(5H,m); 8.2(2H,d); m/e 359 (M+H)+ ; calculated for C20 H26N2O4 : C,67.0;H,7.3;N, 7.8; found: C,67.1;H,7.6;N, 7.7%.

Workup

  1. customevaporated in vacuo
  2. additionA small amount (5 ml) of water was added
  3. extractionthe resulting solution extracted with dichloromethane (3×15 ml)
  4. customdried (PS paper)
  5. customevaporated

Sources & evidence

ORD record
ord-143e335f108f4811b5c1a2ab99e9bb91
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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