Diethyl Ether → N-(5,6,7,8-Tetrahydro-quinolin-8-yl)-butane-1,4-diamine

HRID 1624329Notes

Reaction equation

HRID 1624329 reaction equation
[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O.NN.C(OCC)C>C(O)C>[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

Product 1

HCID 68954262N-(5,6,7,8-Tetrahydro-quinolin-8-yl)-butane-1,4-diamineYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione (15.0 g, 42.98 mmol) dissolved in ethanol (215 ml) was added hydrazine hydrate (13.4 ml). The solution was stirred for 16 hours at room temperature under a N2 atmosphere. A white precipitate formed. Diethyl ether (215 ml) was added and the mixture was stirred for 10 min then filtered and concentrated. Purification via column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v) afforded the product as a brown oil (6.77 g, 74%). 1H NMR (CDCl3) δ 1.57 (m, 9H), 2.05 (m, 2H), 2.75 (m, 6H), 3.78 (t, 1H), 7.06 (dd, 1H, J=7.89, 4.82 Hz), 7.37 (d, 1H, J=7.89 Hz), 8.39 (d, 1H, J=4.82 Hz).

Workup

  1. customA white precipitate formed
  2. stirringthe mixture was stirred for 10 min
  3. filtrationthen filtered
  4. concentrationconcentrated
  5. customPurification via column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v)

Sources & evidence

ORD record
ord-51f747c294ba4cad80b210f7f9ddee64
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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