Triethylamine → 2-(benzylamino)-N-methyl-4-(4-benzoylpiperazin-1-yl)benzamide

HRID 1966459Notes

Reaction equation

HRID 1966459 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]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN.C1COCC1.[CH2:39]([N:41](CC)CC)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[CH2:19][CH2:20][N:21]([C:24](=[O:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:22][CH2:23]2)[CH:15]=[CH:14][C:10]=1[C:11]([NH:41][CH3:39])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 584256602-(Benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acidHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 671818862-(benzylamino)-N-methyl-4-(4-benzoylpiperazin-1-yl)benzamideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (80 mg, 0.2 mmol), 2 M methylamine THF solution (0.96 ml, 1.9 mmol), triethylamine (0.08 ml, 0.57 mmol) and diphenylphosphoryl azide (0.045 ml, 0.2 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-methyl-4-(4-benzoylpiperazin-1-yl)benzamide (30 mg, 36%) was obtained by flash column chromatograph (60% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.97 (d, 3H), 3.14-3.25 (d, br, 4H), 3.65 (s, br, 2H), 3.72 (s, br, 2H), 4.42 (d, 2H), 6.01 (d, J=2.3 Hz, 2H), 6.15 (dd, J=2.3, 8.7 Hz, 1H), 7.26-7.49 (m, 10H), 8.52 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 26.9, 47.8, 48.9, 98.3, 103.4, 107.5, 127.5, 127.6, 129.0, 129.1 130.4, 136.0, 139.7, 151.6, 154.3, 170.6, 170.9.

Workup

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

Sources & evidence

ORD record
ord-b6a417b14e064bf998c826e6e45fc795
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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