Triethylamine → HCID 70606916, compound

HRID 1863122Notes

Reaction equation

HRID 1863122 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].[ClH:15].[Cl:16][CH2:17][C:18]([CH3:25])([OH:24])[CH2:19][NH:20][CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C>[OH-].[Na+]>[ClH:16].[ClH:15].[OH:24][C:18]([CH3:25])([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:17][NH:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6047536-Methoxy-4-methyl-8-quinolinamineHCID 85922240HCID 85922240, compound

Product 1

HCID 70606916HCID 70606916, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred mixture of 10.7 g (0.057 mole) of 8-amino-6-methoxy-4-methylquinoline and 11.7 g (0.057 mole) of 3-chloro-2-methyl-1-(2-propylamino)propan-2-ol, hydrochloride was heated in an oil bath (150°) for 1 hr while 5.8 g (0.057 mole) of triethylamine was added, dropwise. The reaction mixture was stirred at 150° for 24 hrs, cooled, basified with 30 ml of 5% aqueous sodium hydroxide, then extracted with dichloromethane (3×100 ml). The organic extracts were combined, washed with water (2×200 ml), dried over anhydrous magnesium sulfate, then concentrated in vacuo to 50 ml. The solution was chromatographed on a column (60 cm× 7.5 cm) of silica gel (2.5 kg; activity III) using dichloromethane (10 l) followed by methanol-concentrated ammonium hydroxide (25:1) (7 l) as the eluent. The fractions (1 l each) 13-18 were combined then concentrated in vacuo to an oil. The oil was dissolved in ether (100 ml), and the solution was washed with water (2×200 ml), dried over anhydrous magnesium sulfate, then saturated with anhydrous hydrogen chloride. The solid that separated was collected on a filter, dried, then recrystallized from 300 ml of absolute ethanol; yield 4.6 g; mp 232°-234°, dec.

Workup

  1. additionwas added
  2. temperaturecooled
  3. extractionextracted with dichloromethane (3×100 ml)
  4. washwashed with water (2×200 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo to 50 ml
  7. customThe solution was chromatographed on a column (60 cm× 7.5 cm) of silica gel (2.5 kg; activity III)
  8. concentrationThe fractions (1 l each) 13-18 were combined then concentrated in vacuo to an oil
  9. dissolutionThe oil was dissolved in ether (100 ml)
  10. washthe solution was washed with water (2×200 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solid that separated
  13. customwas collected on a filter
  14. customdried
  15. customrecrystallized from 300 ml of absolute ethanol

Sources & evidence

ORD record
ord-b228fd05dc0d4f5e910eebb5d191f21c
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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