tert-butyl N-(4-aminobutyl)carbamate → HCID 69027554, compound

HRID 2383154Notes

Reaction equation

HRID 2383154 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:14]([O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26](Cl)=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[N:29]2)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[C:9]([O:8][C:7](=[O:13])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:26]1[C:25]2[C:30](=[CH:31][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:23][CH:24]=2)[N:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])([CH3:10])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 69027554HCID 69027554, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-(4-aminobutyl)carbamate (28.6 g, 152.0 mmol) was added dropwise to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (40.7 g, 138 mmol), prepared in Parts A-D of Example 1, and triethylamine (38.5 mL, 276 mmol) in dichloromethane over a period of 1.5 hours. After the reaction was stirred for 18 hours, the reaction mixture was washed twice with water and once with saturated aqueous sodium chloride. The organic was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was recrystallized from 2-propanol to afford 51.4 g of tert-butyl[4-(7-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate as a golden brown powder.

Workup

  1. washthe reaction mixture was washed twice with water and once with saturated aqueous sodium chloride
  2. dry with materialThe organic was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-c009623972b94b45b6572d644b3e1974
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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