Ammonium Hydroxide → (+/-)-trans-2-Chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride

HRID 1110703Notes

Reaction equation

HRID 1110703 reaction equation
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[NH:23][C:11]2[CH2:12][C@H:13]3[C@H:18]([CH2:19][C:10]=2[CH:9]=[CH:8]1)[N:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15][CH2:14]3.[NH4+].[OH-]>CN(C)C=O>[ClH:3].[Cl:3][C:7]1[CH:8]=[CH:9][C:10]2[CH2:19][C@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:20][CH2:21][CH3:22])[CH2:12][C:11]=2[N:23]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 18640067(+/-)-trans-2-Oxo-6-propyl-1,2,5,5a,6,7,8,9,9a,10-decahydropyrido[2,3-g]quinoline

Product 1

HCID 18640062(+/-)-trans-2-Chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

Phosphorus oxychloride (272 g, 165 mL, 175 mol) was added over 6 hours to a solution of (±)-trans-2-oxo-6-propyl-1,2,5,5a,6,7,8,9,9a,10-decahydropyrido-[ 2,3-g]quinoline (5.75 g, 23.4 mMol) in dimethylformamide (250 mL) at 135° C. The reaction was stirred at 135° C. for 17 hours, poured over ice, and made basic with NH4OH and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product as a brown oil. Purification by flash chromatography (5% methanol in methylene chloride, 0.5% NH4OH) gave the desired product as a brown oil (5.6 g, 90% yield).

Workup

  1. additionpoured over ice
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product as a brown oil
  6. customPurification by flash chromatography (5% methanol in methylene chloride, 0.5% NH4OH)

Sources & evidence

ORD record
ord-862cfda4e6ad4d039194645781d9de07
Source dataset
uspto-grants-1990_12
Patent number
US04977149

Reaction notes

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