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

HRID 2383110Notes

Reaction equation

HRID 2383110 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>O>[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 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl N-(4-aminobutyl)carbamate (22.01 g, 116.9 mmol) was added to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (36.80 g, 116.9 mmol), prepared in Parts A-D of Example 1, in distilled water. The reaction was heated at 80° C. for 1.5 hours and then stirred at room temperature for four hours. The reaction was not complete, and triethylamine (16 mL, 115 mmol) was added. The reaction was stirred overnight at room temperature. A precipitate formed, which was isolated by filtration and washed with hexanes to provide 39.92 g of tert-butyl[4-(7-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate as a yellow solid.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. customA precipitate formed
  3. customwhich was isolated by filtration
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-d61ae5288608495f919d50db34618e5d
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…