Sodium Hydroxide → HCID 18640059, compound

HRID 1110705Notes

Reaction equation

HRID 1110705 reaction equation
Cl.Cl[C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][C@H:14]3[C@@H:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:16][CH2:17][CH3:18])[CH2:8][C:7]=2[N:19]=1.Br.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+]>O>[CH2:21]([NH:28][C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][C@H:14]3[C@@H:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:16][CH2:17][CH3:18])[CH2:8][C:7]=2[N:19]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 129985681-Phenylmethanamine--hydrogen bromide (1/1)HCID 18640062(+/-)-trans-2-Chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride

Product 1

HCID 18640059HCID 18640059, compoundYield 22.3%

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-octahydropyrido[2,3-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-3e377c687e8b449892d67efdefab0f8b
Source dataset
uspto-grants-1990_12
Patent number
US04977149

Reaction notes

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