1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67377704, compound

HRID 1667249Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]/[C:10](=[N:13]/[H])/[NH:11][OH:12])=[CH:4][CH:3]=1.[O:15]=[C:16]1[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][CH2:18][N:17]1[CH2:34][C:35](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:13]=[C:35]([CH2:34][N:17]3[CH2:18][CH2:19][CH2:20][C:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]3=[O:15])[O:12][N:11]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(Z)-3-(4-Chlorophenyl)-N-hydroxypropanimidamide (0.070 g, 0.352 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.109 g, 0.352 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.135 g, 0.705 mmol) were stirred together in dichloromethane (0.5 mL) at room temperature for 2 hours, then heated to 85° C. overnight. The reaction was cooled, 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 50% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.39-7.04 (m, 14H), 4.83 (s, 2H), 3.54 (t, J=6.5, 2H), 3.11-2.99 (m, 4H), 2.74-2.61 (m, 2H), 1.99-1.76 (m, 2H); MS (ESI+) m/z 472.1 (M+H)+.

Workup

temperatureThe reaction was cooled
washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes

Sources & evidence

ORD record: ord-4e9ebe5db8a74d8ea35a153cb04f0841
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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