N-(2-Aminoethyl)piperidine → HCID 178483553, compound

HRID 2402558Notes

Reaction equation

HRID 2402558 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][N:7]=[C:8]([C:10]1[C:19]2[C:18]([C:20]([OH:22])=[O:21])=[CH:17][C:16](Cl)=[C:15]([C:24]([OH:26])=[O:25])[C:14]=2[C:13]([C:27](=[N:29][NH:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[OH:28])=[CH:12][C:11]=1Cl)[OH:9].[NH2:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>>[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][NH:6][N:7]=[C:8]([C:10]1[C:19]2[C:18]([C:20]([OH:22])=[O:21])=[CH:17][C:16]([NH:39][CH2:40][CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[C:15]([C:24]([OH:26])=[O:25])[C:14]=2[C:13]([C:27](=[N:29][NH:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[OH:28])=[CH:12][C:11]=1[NH:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[OH:9]

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 178483551HCID 178483551, compound

Product 1

HCID 178483553HCID 178483553, compound

Procedure

Compound 7 (45 mg, 0.089 mmol) was suspended in 1-(2-aminoethyl)piperidine (0.5 ml) in a microwave reaction vessel. The tube was flushed with nitrogen, sealed and treated at 150° C. for 10 min in the microwave. The amine was then evaporated off under high vacuum. The crude mixture was purified by HPLC to obtain 8 as a blue solid. Yield 8 (6.62 mg, 0.0096 mmol, 10.8%): 1H NMR (CDCl3) δ: 1.47(m, 4H), 1.64(m, 8H), 1.90(5q, 4H, J=7.3 Hz), 2.26(s, 12H), 2.43(t, 4H, J=7.3 Hz), 2.51(m, 8H), 2.73(t, 4H, J=6.5 Hz), 3.58(m, 4H), 4.22(t, 4H, J=7.5 Hz), 8.07(s, 2H), 9.50(t, 2H, J=4.9 Hz); 13C NMR (CDCl3) δ: 24.44(2×CH2), 26.06(4×CH2, 2×CH2), 38.66(2×CH2), 40.49(2×CH2), 45.34(4×CH2), 54.57(4×CH3), 57.29(2×CH2), 57.38(2×CH2), 101.97(2×C), 118.38(2×CH), 121.07(2×C), 125.62(2×C), 148.90(2×C), 163.05(2×C═O), 165.79(2×C═O); HRMS (ES+) calcd C38H56N8O4 [M+2H]2+ 345.2285. Found: 345.2293.

Workup

  1. customThe tube was flushed with nitrogen
  2. customsealed
  3. additiontreated at 150° C. for 10 min in the microwave
  4. customThe amine was then evaporated off under high vacuum
  5. customThe crude mixture was purified by HPLC

Sources & evidence

ORD record
ord-3581b19549684ab58687a456e45d7451
Source dataset
uspto-grants-2014_08
Patent number
US08796456B2

Reaction notes

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