1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 135883266, compound

HRID 1667243Notes

Reaction equation

HRID 1667243 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:11])/[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[O:12]=[C:13]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH2:15][N:14]1[CH2:31][C:32](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[N:11]=[C:32]([CH2:31][N:14]3[CH2:15][CH2:16][CH2:17][C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:13]3=[O:12])[O:1][N:2]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acidHCID 1355853864,N-DIHYDROXY-BENZAMIDINE

Product 1

HCID 135883266HCID 135883266, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

(Z)—N′,4-Dihydroxybenzimidamide (0.251 g, 1.649 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.510 g, 1.649 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.474 g, 2.473 mmol) were stirred together in dichloroethane at room temperature for 2 hours, then heated to 85° C. for 16 hours. The reaction was cooled and concentrated. The residue was dissolved in dichloromethane (5 mL) and washed with water (3 mL). The organic layer was concentrated and the residue was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.95-7.78 (m, 2H), 7.40-7.16 (m, 10H), 6.85-6.71 (m, 2H), 5.93 (s, 1H), 4.88 (s, 2H), 3.64 (t, J=6.5, 2H), 2.78-2.66 (m, 2H), 1.99-1.80 (m, 2H); MS (ESI+) m/z 426.1 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  4. washwashed with water (3 mL)
  5. concentrationThe organic layer was concentrated
  6. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-6ec0dd254f784099a3d125f30ebdb905
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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