Dichloromethane → {4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl ester

HRID 1696851Notes

Reaction equation

HRID 1696851 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(Cl)Cl>C(O)C>[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 66860915(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester

Product 1

HCID 58100085{4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl esterYield 206.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 59 (4.0 g, 8.20 mmol) and hydrazine (2.06 g, 41.20 mmol) dissolved in ethanol (50 mL) and methylene chloride (10 mL) was heated to reflux. The reaction mixture was allowed to stir for 16 h under N2 atmosphere. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane to afford the desired product 7 (6.00 g, 72%) as an off white solid: 1H NMR (300 MHz, CDCl3) δ 7.34 (s, 4H), 7.07 (s, 4H), 5.08 (s, 2H), 3.18 (t, 2H), 2.94 (s, 2H), 2.70 (t, 2H), 2.59 (t, 4H), 1.65-1.47 (m, 5H); m/z (ESI) 355 [C22H30N2O2+H]+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography
  4. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane

Sources & evidence

ORD record
ord-6707dc3f65424cb5b3195ce19164ad24
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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