Butylamine → HCID 44481974, compound

HRID 1972127Notes

Reaction equation

HRID 1972127 reaction equation
[C:1]1([CH:7]2[C:16]3[C:11]4=[C:12]([CH:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:21][CH2:22][N:10]4[CH2:9][CH2:8]2)[CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:29]([NH2:33])[CH2:30][CH2:31][CH3:32].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH2:29]([NH:33][C:17]([C:14]1[CH:15]=[C:16]2[C:11]3=[C:12]([CH:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:21][CH2:22][N:10]3[CH2:9][CH2:8][CH:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=1)=[O:19])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58452952HCID 58452952, compound

Product 1

HCID 44481974HCID 44481974, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carboxylic acid (14), (189 mg, 0.512 mmol) in dichloromethane (10 mL) were added butyl amine (0.027 mL, 0.512 mmol), EDCl (196 mg, 1.02 mmol), followed DMAP (4-(Dimethylamino)pyridine) (70 mg, 1.02 mmol) under argon at 0° C. The reaction mixture was then stirred at room temperature for overnight. The reaction was quenched with water (30 mL). The residue was isolated in a typical aqueous workup and purified by MPLC (medium pressure liquid chromatography) using silica gel column with 25 to 30% EtOAc:Hexane to give N-butyl-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carboxamide (481), (113 mg 52%). 1H NMR (300 MHz, CDCl3) ppm 1H NMR (300 MHz, Solvent) ppm 0.87 (t, J=6.0 Hz, 3H) 1.17-1.38 (m, 2H) 1.36-1.52 (m, 2H) 2.03-2.17 (m, 2H) 2.18-2.36 (m, 2H) 3.06-3.37 (m, 6H) 4.21 (t, J=5.27 Hz, 2H) 5.61-5.75 (m, 1H) 7.03-7.16 (m, 4H) 7.17-7.37 (m, 8H).

Workup

  1. customat 0° C
  2. customThe reaction was quenched with water (30 mL)
  3. customThe residue was isolated in a typical aqueous workup
  4. custompurified by MPLC (medium pressure liquid chromatography)

Sources & evidence

ORD record
ord-c8131ba6b1124523a16259c27a1dc9d1
Source dataset
uspto-grants-2013_04
Patent number
US08431702B2

Reaction notes

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