1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45275801, compound

HRID 1667084Notes

Reaction equation

HRID 1667084 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:12]=[C:13]1[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31](O)=[O:32].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:32]=[C:31]([N:9]1[CH2:10][CH2:11][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8]1)[CH2:30][N:14]1[CH2:15][CH2:16][C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]1=[O:12]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31467433-PhenylpyrrolidineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275801HCID 45275801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-phenylpyrrolidine (0.029 g, 0.194 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.052 g, 0.176 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.051 g, 0.244 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.43 (m, 15H), 4.09-4.22 (m, 2H), 3.63-4.11 (m, 2H), 3.26-3.63 (m, 5H), 2.77-2.89 (m, 2H), 2.22-2.42 (m, 1H), 1.91-2.13 (m, 1H); MS (ESI+) m/z 425 (M+H)+.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-ef3ab2bf8f7a4ca3bb75cdce1b43d84d
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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