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 899827Notes

Reaction equation

HRID 899827 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, 1H), 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-97d9ccda5a6d465592f17bf53f67ff3f
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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