Sodium Hydroxide → HCID 18640059, compound

HRID 345297Notes

Reaction equation

HRID 345297 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Br.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>O>[CH2:13]([NH:20][C:3]1[CH:4]=[CH:5][C:9]2[CH2:10][C@H:11]3[C@@H:6]([CH2:5][CH2:4][CH2:3][N:2]3[CH2:7][CH2:6][CH3:11])[CH2:7][C:8]=2[N:2]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68264Quinoline hydrochlorideHCID 129985681-Phenylmethanamine--hydrogen bromide (1/1)

Product 1

HCID 18640059HCID 18640059, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of (±)-trans-2-chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido2,3-g]quinoline hydrochloride (2.27 g, 7.50 mmol) and benzylamine hydrobromide (15.0 g) was heated to 240° C. to form a brown, molten semi-solid. After 15 minutes, the molten semi-solid was poured into water, made basic with dilute NaOH solution, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give a brown oil. Purification by flash chromatography (6% methanol in methylene chloride, NH4OH) provided (±)-trans-2-benzylamino-6-propyl-5,5a, 6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline (Rf=0.35, 561 mg, 22% yield) as a brown oil.

Workup

  1. customto form a brown, molten semi-solid
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customPurification by flash chromatography (6% methanol in methylene chloride, NH4OH)

Sources & evidence

ORD record
ord-2e54b65c251a4a7e9c4e479724f2ac5d
Source dataset
uspto-grants-1991_10
Patent number
US05057515

Reaction notes

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