tert-butyl N-(4-aminobutyl)carbamate → HCID 86626162, compound

HRID 2383146Notes

Reaction equation

HRID 2383146 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39]>ClCCl.NCCCCNC(=O)OC(C)(C)C>[C:38]([O:37][C:36](=[O:42])[NH:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[N:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])([CH3:41])([CH3:39])[CH3:40]

Participants

6

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 670509926-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 86626162HCID 86626162, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-benzyloxy-4-chloro-3-nitroquinoline (14.47 g, 46.29 mmol), prepared in Parts A-D of Example 57, and triethylamine (8.4 mL, 60.2 mmol) in dichloromethane (200 mL) was cooled to 0° C. tert-Butyl N-(4-aminobutyl)carbamate (8.71 g, 46.3 mmol) was added; the reaction was stirred for 15 minutes at 0° C. and then allowed to warm to ambient temperature and stirred for five hours. An analysis by TLC indicated the presence of starting material; therefore, additional tert-butyl N-(4-aminobutyl)carbamate (0.5 mL, 2.6 mmol) was added. The reaction was stirred overnight and then washed with water (2×200 mL). The combined washings were extracted with chloroform after the addition of sodium chloride. The combined organic solutions were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate (100 mL). The crystals were isolated by filtration and washed with cold hexanes to provide 17.62 g of tert-butyl[4-(6-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate as an orange powder.

Workup

  1. additionwas added
  2. temperatureto warm to ambient temperature
  3. stirringstirred for five hours
  4. stirringThe reaction was stirred overnight
  5. washwashed with water (2×200 mL)
  6. extractionThe combined washings were extracted with chloroform
  7. additionafter the addition of sodium chloride
  8. dry with materialThe combined organic solutions were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was recrystallized from ethyl acetate (100 mL)
  12. customThe crystals were isolated by filtration
  13. washwashed with cold hexanes

Sources & evidence

ORD record
ord-7beeb7d4012e4500967fac35b6a1db7d
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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