Ethylamine hydrochloride → HCID 46199220, compound

HRID 1966462Notes

Reaction equation

HRID 1966462 reaction equation
[CH2:1]([NH:8][C:9]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:33]([NH2:35])[CH3:34].CCN(C(C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH2:1]([NH:8][C:9]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:19]2)[CH:15]=[CH:14][C:10]=1[C:11]([NH:35][CH2:33][CH3:34])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 584256602-(Benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid

Product 1

HCID 46199220HCID 46199220, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (50 mg, 0.12 mmol), ethylamine hydrochloride (36 mg, 0.36 mmol), DIPEA (0.20 ml, 1.2 mmol) and diphenylphosphoryl azide (0.026 ml, 0.12 mmol) in 15 ml THF was stirred for 16 hours. The run was quenched with 1 ml water and all the solvents were evaporated under vacuum. 2-(benzylamino)-N-ethyl-4-(4-benzoylpiperazin-1-yl)benzamide (15 mg, 33%) was obtained by flash column chromatograph (60% ethyl acetate in hexanes), and its hydrochloride was made by bubbling HCL gas in ether solution. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 1.10 (t, J=7.2 Hz, 3H), 3.19-3.47 (m, br, 10H), 4.40 (s, 2H), 6.43 (t, J=8.3 Hz, 2H), 7.27-7.59 (m, 13H), 8.26 (s, 1H). 13C NMR (125 MHz, DMSO-d6): δ (ppm) 14.8, 33.6, 47.5, 127.0, 127.2, 127.8, 128.4, 128.5, 129.4, 129.6, 135.7, 168.3, 169.0.

Workup

  1. customThe run was quenched with 1 ml water and all the solvents
  2. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-604085c5ccd24292b772a69af31ed450
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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