Trifluoroacetic acid → Allyl-methyl-[4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-butyl]-amine

HRID 2212514Notes

Reaction equation

C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:25][CH:26]=[CH2:27])[CH3:24])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:25]([N:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[NH:8][CH2:9][CH2:10][CH2:11]2)[CH:26]=[CH2:27]

Participants

Conditions

Temperature: 40 °C

Procedure

3.64 g (9.7 mmol) 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 5 ml CH2Cl2 were treated with 3.5 ml TFA at 0° C., and the solution was stirred at 40° C. for 1 h. The solution was concentrated and the residue dissolved in a mixture of a saturated aqueous solution of NaHCO3 and ether. The inorganic phase was extracted with ether and the combined organic phases were washed with water and dried over Na2SO4 to yield 1.85 g (69%) Allyl-methyl-[4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-butyl]-amine, MS: 275 (MH+).

Workup

concentrationThe solution was concentrated
dissolutionthe residue dissolved in a mixture of a saturated aqueous solution of NaHCO3 and ether
extractionThe inorganic phase was extracted with ether
washthe combined organic phases were washed with water
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-c0f95c27d5384d7999553989584348d1
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102007B2

Reaction notes

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