Triethylamine → Benzyl 4-aminophenethylcarbamate

HRID 2399864Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)(Cl)Cl>[C:23]1([CH2:22][O:21][C:19](=[O:20])[NH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5.00 g (36.7 mmol) of 2-(4-aminophenyl)ethylamine in 100 mL of chloroform was cooled to 0° C. and 3.72 g (5.20 mL, 36.8 mmol) of triethylamine was added. A solution of 6.26 g (5.2 mL, 36.8 mmol) of benzyl chloroformate in 40 mL of chloroform was then added dropwise over a 30-min period. The reaction was allowed to stir at 0° C. for 2 h. It was diluted with 100 mL of chloroform, washed with 100-mL portions of water and brine, dried over sodium sulfate and concentrated. The residue was dissolved in 50% ethyl acetate/hexane and stirred with 30 g of silica gel, filtered, and concentrated. Further purification by recrystallization from ethyl acetate/hexanes gave 4.82 g (49%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) 7.33 (s, 5H), 6.94 (d, 2H, J= 8.2 Hz), 6.60 (d, 2H, J=8.2 Hz), 5.07 (s, 2H), 4.84 (broad s, 1H), 3.55 (broad s, 2H), 3.37 (m, 2H), 2.67 (t, 2H, J=6.9 Hz). FAB MS m/z 271 (M+1).

Workup

washwashed with 100-mL portions of water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated
dissolutionThe residue was dissolved in 50% ethyl acetate/hexane
stirringstirred with 30 g of silica gel
filtrationfiltered
concentrationconcentrated
customFurther purification
customby recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-53696c14d79d4e8fa256ed41d744660a
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05451677

Reaction notes

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