Hydrochloric Acid → HCID 19019400, compound

HRID 2081674Notes

Reaction equation

HRID 2081674 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:11](=[O:33])[CH:10]=[C:9]1OCO)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][Cl:44].[ClH:46].O.CN(C)[CH:50]=[O:51]>C(OCC)(=O)C.CC(O)C.C(OCC)C>[ClH:44].[ClH:46].[CH2:1]([N:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:11](=[O:33])[CH:10]=[C:9]1[CH2:50][O:51][CH2:43][CH2:42][CH2:41][N:40]([CH3:45])[CH3:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 19019370HCID 19019370, compound

Product 1

HCID 19019400HCID 19019400, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.2 g (15 mMole) 1-Benzyl-2-hydroxymethoxy-5-octadecyloxy-4(1H)-pyridone are dissolved in 110 mL anhydrous dimethylformamide at 70° C. and mixed portionwise with 0.60 g (20 mMole) sodium hydride (80% in paraffin oil). After subsequently stirring for 1.5 hours at 70° to 80° C., a solution of 3.3 g (27.15 mMole) 3-dimethylaminopropyl chloride in 20 mL anhydrous dimethylformamide is added dropwise thereto. The reaction mixture is then stirred for 2 hours at 70° C. Thereafter, the solution is evaporated to dryness under vacuum and the residue is mixed with water and dichloromethane. The organic phase is separated off, dried over anhydrous sodium sulphate and evaporated. The residue is chromatographed on a column of silica gel with dichloromethane/methanol saturated with gaseous ammonia (97:3 v/v), an oily substance being obtained. 1.8 g (3.3 mMole) of this substance are dissolved in a mixture of 30 mL ethyl acetate and 3,5 mL propan-2-ol and mixed with diethyl ether saturated with gaseous hydrogen chloride for salt formation. The precipitated salt is recrystallized from ethyl acetate/propan-2-ol (3:1 v/v), colorless crystals being obtained; m.p. 155°-159° C. The solid material contains about 1/4 mole of water per mole of the said product.

Workup

  1. stirringThe reaction mixture is then stirred for 2 hours at 70° C
  2. customThereafter, the solution is evaporated to dryness under vacuum
  3. additionthe residue is mixed with water and dichloromethane
  4. customThe organic phase is separated off
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on a column of silica gel with dichloromethane/methanol saturated with gaseous ammonia (97:3 v/v)
  8. customan oily substance being obtained
  9. customThe precipitated salt is recrystallized from ethyl acetate/propan-2-ol (3:1 v/v), colorless crystals
  10. custombeing obtained

Sources & evidence

ORD record
ord-3cf0e291c80c4eb2bb667129dc61c11e
Source dataset
uspto-grants-1993_02
Patent number
US05185352

Reaction notes

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