Triethylamine → 6-Methoxy-8-[6-phthalimidohexylamino]lepidine

HRID 1863125Notes

Reaction equation

HRID 1863125 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].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C(N(CC)CC)C>CC(C)=O>[CH3:14][O:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([NH:1][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:26](=[O:27])[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=[O:32])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141120N-(6-Bromohexyl)phthalimideHCID 6047536-Methoxy-4-methyl-8-quinolinamine

Product 1

HCID 6086466-Methoxy-8-[6-phthalimidohexylamino]lepidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 20.9 g (0.111 mole) of 8-amino-6-methoxy-4-methylquinoline and 34.5 g (0.111 mole) of N-(6-bromohexyl)phthalimide was heated in an oil bath (130° ) while 11.2 g (15.4 ml; 0.111 mole) of triethylamine was added dropwise over a period of 45 minutes. The temperature of the bath was kept at 130° for 60 minutes, at 150° for 60 minutes, between 150° and 190° for 30 minutes, and at 190° for 30 minutes. The mixture was cooled then diluted with acetone (100 ml). The precipitate as collected on a filter, washed with acetone (2×50 ml), dried, then discarded. The filtrate was concentrated in vacuo to a dark oil; yield 53 g. The oil was dissolved in 100 ml of dischloromethane, and the solution was chromatographed on a column (40 cm× 8 cm dia) of silica gel (1000 g; activity III) using dichloromethane (1.5 l) as the eluent. Fractions containing the product were combined then concentrated in vacuo; yield 35.5 g (83.7%). That material was satisfactory for conversion to the target compound, however a 93% recovery of analytically pure material (mp 84°-85° ) could be obtained by crystallization from ethanol.

Workup

  1. additionwas added dropwise over a period of 45 minutes
  2. waitat 190° for 30 minutes
  3. temperatureThe mixture was cooled
  4. customThe precipitate as collected on a filter
  5. washwashed with acetone (2×50 ml)
  6. customdried
  7. concentrationThe filtrate was concentrated in vacuo to a dark oil
  8. dissolutionThe oil was dissolved in 100 ml of dischloromethane
  9. customthe solution was chromatographed on a column (40 cm× 8 cm dia) of silica gel (1000 g; activity III)
  10. additionFractions containing the product
  11. concentrationwere combined then concentrated in vacuo

Sources & evidence

ORD record
ord-b7a6ad0cd1ed4b50822a13f2b0d13391
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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