Acetyl chloride → Trans-(+/-)-2-acetylamino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline

HRID 485676Notes

Reaction equation

HRID 485676 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:17]=1.[O:18]1CC[CH2:20][CH2:19]1.C(Cl)(=O)C>CN(C)C=O.CCOCC>[C:19]([NH:1][C:2]1[S:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:17]=1)(=[O:18])[CH3:20]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 13491309trans-(+/-)-2-Amino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline

Product 1

HCID 18599019Trans-(+/-)-2-acetylamino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinolineYield 30.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution was prepared from 0.15 g. of trans-(±)-2-amino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline (from Example 1) in 3 ml. of tetrahydrofuran (THF) to which has been added two drops of dimethylformamide (DMF). Five hundredths milliliters of acetyl chloride were added and the solution stirred at room temperature for 15 minutes. In time, the reaction mixture became a solid colorless mass. The solid was suspended in ether and the ethereal suspension filtered. The solid was then recrystallized from a methanol/ether solvent mixture to give purified trans-(±)-2-acetylamino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline hydrochloride; yield=30.3%; melting point above 200° C.

Workup

  1. customA solution was prepared from 0.15 g
  2. filtrationthe ethereal suspension filtered
  3. customThe solid was then recrystallized from a methanol/ether solvent mixture
  4. customto give
  5. custompurified trans-(±)-2-acetylamino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline hydrochloride

Sources & evidence

ORD record
ord-72ea882ea2514dae82e9df00c53157ea
Source dataset
uspto-grants-1985_08
Patent number
US04537893

Reaction notes

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