Hydrochloric Acid → HCID 17883740, compound

HRID 2350931Notes

Reaction equation

HRID 2350931 reaction equation
[CH3:1][N:2]([CH:14]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[C:18]1=[O:31])[CH2:15][CH3:16])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH3:13].[ClH:32].O1CCC[CH2:34]1>>[ClH:32].[CH3:1][N:2]([CH:14]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[C:18]1=[O:31])[CH2:15][CH3:16])[CH2:3][C:12]1[C:7]2[C:8](=[CH:13][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][C:11]=1[CH3:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 53688300HCID 53688300, compound

Product 1

HCID 17883740HCID 17883740, compound

Procedure

To a solution of 1.3 g (3 mmol) of 2-[N-methyl-N-(2-methyl-naphth-1-yl)-amino-prop-3-yl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one in 50 ml of tetrahydrofuran, 4.5 ml of a 1 molar borane-tetrahydrofuran complex in tetrahydrofuran are added and 0.55 ml (4.5 mmol) of boron trifluoride-diethyl etherate complex are added dropwise with stirring at ambient temperature. After 3 hours' reaction time, 5 ml of 6 molar hydrochloric acid are added dropwise, the mixture is refluxed for 0.5 hours and then the solvent is evaporated off in vacuo. The aqueous portion remaining is made alkaline with 2 molar sodium hydroxide solution and extracted with methylene chloride. The organic phase is washed with water, dried over sodium sulphate, evaporated down in vacuo and purified over a silica gel column (0.063-0.2 mm) with methylene chloride and then with increasing amounts of ethanol (up to 5%). The hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid and is then recrystallised from acetone.

Workup

  1. additionare added dropwise
  2. temperaturethe mixture is refluxed for 0.5 hours
  3. customthe solvent is evaporated off in vacuo
  4. extractionextracted with methylene chloride
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated down in vacuo
  8. custompurified over a silica gel column (0.063-0.2 mm) with methylene chloride
  9. customThe hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid
  10. customis then recrystallised from acetone

Sources & evidence

ORD record
ord-6ed5b76615634e3bae54b25f45f6ecfb
Source dataset
uspto-grants-1989_10
Patent number
US04871735

Reaction notes

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