Triethylamine → [3-(Isopropylhydrazono)-propyl]-carbamic acid benzyl ester

HRID 606617Notes

Reaction equation

HRID 606617 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH:19]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(CC)CC>C(O)(C)C>[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH:19]=[N:6][NH:5][CH:2]([CH3:4])[CH3:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 10398106Benzyl (3-Oxopropyl)carbamate

Product 1

HCID 67047463[3-(Isopropylhydrazono)-propyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of isopropylhydrazine hydrochloride (92.4 g, 0.84 mol) and (3-oxo-propyl)-carbamic acid benzyl ester (173 g, 0.84 mol) in isopropyl alcohol (1.7 L) was added Et3N (140 mL, 1.0 mol) over 20 min. The resulting slurry was heated at reflux for 3 h, and then was cooled to rt and concentrated. The residue was partitioned between EtOAc (700 mL) and water (700 mL). The organic layer was washed with water (3×500 mL), satd. aq. NaCl (300 mL), dried (MgSO4), and concentrated to afford the title compound. The crude product was used in next reaction without purification. MS (ESI): exact mass calcd. for C14H21N3O2, 263.16; m/z found, 264.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.36-7.25 (m, 5H), 7.02 (t, J=4.5, 1H), 5.10 (br s, 1H), 5.09 (s, 2H), 3.45-3.34 (m, 3H), 2.40-2.34 (m, 2H), 1.11 (d, J=6.4, 6H).

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated
  4. customThe residue was partitioned between EtOAc (700 mL) and water (700 mL)
  5. washThe organic layer was washed with water (3×500 mL)
  6. dry with materialaq. NaCl (300 mL), dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9177cd9618114306b3e282b2ab570536
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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