Acetic Acid → HCID 58689747, compound

HRID 577795Notes

Reaction equation

HRID 577795 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[NH2:17][CH2:18][C:19]1[C:20]([N:29]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:30][CH3:31])=[N:21][C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[CH:28]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:17][CH2:18][C:19]1[C:20]([N:29]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:30][CH3:31])=[N:21][C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[CH:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58689760HCID 58689760, compound

Product 1

HCID 58689747HCID 58689747, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-bis-trifluoromethyl benzaldehyde (0.185 g, 0.76 mmol) in MeOH (3 mL) was added (3-aminomethyl-5,6,7,8-tetrahydro-quinoline-2-yl)-cyclopentylmethyl-ethylamine (0.2 g, 0.69 mmol), followed by the addition of acetic acid (0.08 mL, 1.39 mmol). This reaction mixture was stirred at RT for 1 h, after which time sodium cyanoborohydride (0.172 g, 2.78 mmol) was added, and stirring was continued for another 8 h. The solvent was then evaporated under vacuum and water was added, followed by extraction of the product with ethyl acetate. The organic layer was washed with saturated sodium bisulfite solution, the organic layer was separated and dried over sodium sulfate, and the solvent was evaporated to give the {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-5,6,7,8-tetrahydro-quinolin-2-yl}-cyclopentylmethyl-ethyl amine (0.250 g), yield: 70%.

Workup

  1. stirringstirring
  2. waitwas continued for another 8 h
  3. customThe solvent was then evaporated under vacuum and water
  4. additionwas added
  5. extractionfollowed by extraction of the product with ethyl acetate
  6. washThe organic layer was washed with saturated sodium bisulfite solution
  7. customthe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-eb4154be7ed14810b9e5adb78b67bee9
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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