tert-butyl N-(4-aminobutyl)carbamate → HCID 86684852, compound

HRID 2369473Notes

Reaction equation

HRID 2369473 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25].C(N(CC)CC)C>O1CCCC1>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:19]1[CH:20]=[CH:15][C:16]([N+:24]([O-:26])=[O:25])=[CH:17][C:18]=1[N+:21]([O-:23])=[O:22])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 6264DinitrofluorobenzeneHCID 8471Triethylamine

Product 1

HCID 86684852HCID 86684852, compoundYield 149.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-Boc-1,4-butanediamine (0.400 g; 2.12 mmol) and 1-fluoro-2,4-dinitrobenzene (280 μL; 2.23 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) was added triethylamine (886 μL; 6.36 mmol). The reaction solution was stirred at ambient temperature for 17 hours and was then concentrated. The residue was dissolved in ethyl acetate and washed with water, saturated NaHCO3 and saturated NaCl. The organic solution was dried over MgSO4 and concentrated to give a yellow oil (1.12 g). Purification using a Thomson Instruments Single StEP™ silica gel column (25 g) and eluting with 20% ethylacetate/80% hexanes followed by 50% ethyl acetate/50% hexanes produced the product as a yellow oil (0.751 g, 100%). 1H NMR (d6-DMSO) 1.36 (9H, s), 1.44 (2H, m) 1.58 (2H, m), 2.93 (2H, m), 3.46 (2H, m), 6.82 (1H, t, J=5.6 Hz), 7.23 (1H, d, J=9.5 Hz), 8.27 (1H, dd, J=2.7 Hz, J=9.6 Hz), 8.85 (2H, m).

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, saturated NaHCO3 and saturated NaCl
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c99cd29c953a420ca1c31869d27a24cc
Source dataset
uspto-grants-2014_04
Patent number
US08703907B2

Reaction notes

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