Toluene → HCID 136005590, compound

HRID 1350520Notes

Reaction equation

HRID 1350520 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22](N)=[N:21][C:20]=2[CH:31]=1.C1(C)C=CC=CC=1>CS(C)=O>[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:22]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[NH:25][C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[CH:31][C:20]=3[N:21]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 20760001(S)-2-BenzylpiperazineHCID 135797752HCID 135797752, compound

Product 1

HCID 136005590HCID 136005590, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 3-(S)-benzyl-piperazine (800 mg, 4.5 mmol), 8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (424 mg, 1.5 mmol), toluene (8 mL), dimethylsulfoxide (2 mL) and reflux for 3 days. Concentrate and pour into water (50 mL), filtrate the resulting solid, redissolve in dichloromethane (200 mL), wash with water and dry over magnesium sulfate. After concentration, purify by flash chromatography (dichloromethane then gradient of methanol 3–10%) to give (316 mg, 53%) of the title compound as a yellow foam: mp 79–92° C.; 1H NMR (CDCl3): δ 2.59 (dd, 1H), 2.90–2.66 (m, 3H), 3.09–2.94 (m, 3H), 3.85 (bm, 1H), 4.03 (bm, 1H), 4.88 (s, 1H), 6.61 (dd, 1H), 6.79–6.84 (m, 2H), 6.97 (t, 1H), 7.06 (t, 1H), 7.35–7.19 (m, 7H); MS (APCI) m/z (rel intensity) 403.4 (100).

Workup

  1. concentrationConcentrate
  2. additionpour into water (50 mL), filtrate the resulting solid
  3. dissolutionredissolve in dichloromethane (200 mL)
  4. washwash with water
  5. dry with materialdry over magnesium sulfate
  6. concentrationAfter concentration
  7. custompurify by flash chromatography (dichloromethane

Sources & evidence

ORD record
ord-84e6a156bf394974b884eb683dc38f4e
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…