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

HRID 49480
Notes
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Reaction equation

HRID 49480 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 695154176-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 21966617Allyl-methyl-[4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-butyl]-amineYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-ec7fca52db6d439b85b45fc3d6bb3257
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706751B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes