Acetic Acid → Tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

HRID 1943026Notes

Reaction equation

HRID 1943026 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]=O)[C:3]1=[O:14].[NH2:15][CH2:16][CH:17]([CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:15][CH2:16][CH:17]([CH:24]2[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]1=[O:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58415947Tert-butyl 4-(2-amino-1-phenylethyl)piperidine-1-carboxylate

Product 1

HCID 58415941Tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (0.590 g, 3.15 mmol), tert-butyl 4-(2-amino-1-phenylethyl)piperidine-1-carboxylate (1.2 g crude, 3.94 mmol), and acetic acid (0.677 ml, 11.83 mmol) were combined in CH2Cl2 (20 ml). Sodium triacetoxyborohydride (2.506 g, 11.83 mmol) was added and the reaction stirred for 16 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The product was carried on without further purification.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb, the aqueous portion extracted 3×CH2Cl2
  3. dry with materialthe organic portion dried (Na2SO4)
  4. concentrationthen concentrated in vacuo
  5. customThe product was carried on without further purification

Sources & evidence

ORD record
ord-0353f2fd653b48548302c70aa6a7fef7
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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