1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45275698, compound

HRID 1667089Notes

Reaction equation

HRID 1667089 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:19]=[C:20]1[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:22][N:21]1[CH2:37][C:38](O)=[O:39].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH2:9][N:10]([C:38](=[O:39])[CH2:37][N:21]3[CH2:22][CH2:23][C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:20]3=[O:19])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28232394,4-DiphenylpiperidineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275698HCID 45275698, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4-diphenylpiperidine (Matrix, 0.48 mg, 2.00 mmol) in dichloromethane was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.59 g, 2.00 mmol) under nitrogen. To the reaction was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.77 g, 4.00 mmol) and N,N-dimethylpyridin-4-amine (0.024 g, 0.20 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate:water (8:2). The organic layer was separated, washed with water and then brine, dried over MgSO4, filtered, and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.25-7.37 (m, 12H), 7.14-7.24 (m, 8H), 4.20 (s, 2H), 3.61-3.67 (m, 2H), 3.50 (t, J=6.4 Hz, 2H), 3.42-3.47 (m, 2H), 2.80 (t, J=6.6 Hz, 2H), 2.35-2.41 (m, 2H), 2.26-2.31 (m, 2H); MS (DCI+) m/z 515 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned in ethyl acetate:water (8:2)
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-a4a8c9a695c742db81e35f4fdaec15f4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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