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

HRID 1110707Notes

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

Participants

Conditions

Temperature: 210 °C

Procedure

A mixture of (±)-trans-2-chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride (2.50 g, 8.3 mmol) and pyrrolidine hydrochloride (10 g) was heated to 210° C. to form a homogeneous molten semi-solid. After 45 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 the crude product as a brown solid. Purification by flash chromatography (10% methanol in methylene chloride, NH4OH) provided (±)-trans-2-pyrrolidino-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline (Rf =0.45, 1.32 g, 53% yield) as a brown oil.

Workup

customto form a homogeneous molten semi-solid
extractionextracted with methylene chloride
dry with materialThe extract was dried (Na2SO4)
concentrationconcentrated
customto give the crude product as a brown solid
customPurification by flash chromatography (10% methanol in methylene chloride, NH4OH)

Sources & evidence

ORD record: ord-2b861294b5d04ef0b9ffaf58577a3838
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04977149

Reaction notes

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