Hydrazine hydrate (1:1) → N1-(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

HRID 1624323Notes

Reaction equation

HRID 1624323 reaction equation
[CH3:1][C:2]1[C:37]([CH3:38])=[CH:36][C:5]2[NH:6][C:7]([CH2:9][N:10]([CH:26]3[C:35]4[N:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH2:29][CH2:28][CH2:27]3)[CH2:11][CH2:12][CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)=[N:8][C:4]=2[CH:3]=1.O.NN>C(O)C.C(OCC)C>[CH3:38][C:37]1[C:2]([CH3:1])=[CH:3][C:4]2[NH:8][C:7]([CH2:9][N:10]([CH:26]3[C:35]4[N:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH2:29][CH2:28][CH2:27]3)[CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[N:6][C:5]=2[CH:36]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 691776612-{4-[(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

Product 1

HCID 59694186N1-(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamineYield 40.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-{4-[(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione (60 mg, 0.118 mmol) in ethanol (2.5 mL) was added hydrazine hydrate (0.05 mL, 1.03 mmol) and the mixture stirred at room temperature for 16 hours. The mixture was then diluted with diethyl ether, dried (MgSO4), filtered and concentrated under reduced pressure to give a crude yellow oil. The oil was purified by flash chromatography (1.75 cm ID, 12 g silica, 10:1:1 CH2Cl2:MeOH:NH4OH) to give pure N1-(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (18 mg, 38%). 1H NMR (CDCl3) δ 1.30-1.46 (m, 4H), 1.60-1.75 (m, 1H), 1.82-1.96 (m, 1H), 1.98-2.08 (m, 11−1), 2.14-2.24 (m, 1H), 2.35 (s, 6H), 2.47-2.59 (m, 3H), 2.65-2.90 (m, 3H), 3.92-4.06 (m, 3H), 7.13 (dd, 1H, J=7.9, 4.8 Hz), 7.34 (s, 2H), 7.40 (d, 1H, J=7.1 Hz), 8.58 (s, 1H, J=3.5 Hz).

Workup

  1. dry with materialdried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude yellow oil
  5. customThe oil was purified by flash chromatography (1.75 cm ID, 12 g silica, 10:1:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-803884f32e0c43078f71b390ab71edd8
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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