tert-butyl N-(4-aminobutyl)carbamate → HCID 18783946, compound

HRID 1108635Notes

Reaction equation

HRID 1108635 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(N(CC)CC)C>[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 18783946HCID 18783946, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.72 g (2.97 mmol) of 2,4-Dichloro-3-nitroquinoline and 0.56 g (2.97 mmol) of N-(tert-butoxycarbonyl)-1,4-diaminobutane were heated in 12 ml of triethylamine at 70° C. and stirred for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in methylene chloride, washed with water, and dried (MgSO4). The solvent was distilled off under reduced pressure. The residue was triturated with n-hexane-diethyl ether (1:1 (v/v)) and collected by filtration to obtain 0.97 g (2.46 mmol) of 4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline shown below as yellow powder (mp: 125-126.5° C.). ##STR41## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3340, 3280, 1680, 1540, 1520. 1H-NMR (CDCl3) δ (ppm) :1.46 (9H, s), 1.63 (2H, m), 1.78 (2H, m), 3.19 (2H, q, J=6.4 Hz), 3.47 (2H, q, J=61 Hz), 4.68 (1H, br), 6.41 (1H, b r), 7.52 (1H, t, J=7.7 Hz), 7.74 (1H, t, J=7.8 Hz), 7.91 (1H, d, J=8.4 Hz), 8.11 (1H, d, J=8.4 Hz).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was triturated with n-hexane-diethyl ether (1:1 (v/v))
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-887d4551a9294201865f94c4463b0900
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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