Sodium Hydroxide → 1-(Benzyloxy)but-3-en-2-amine hydrochloride

HRID 595327Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]([NH:13]C(=O)C(Cl)(Cl)[Cl:16])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[ClH:16].[CH2:1]([O:8][CH2:9][CH:10]([NH2:13])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-[1-(benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide (7.5 g, 23 mmol) and sodium hydroxide (4.0 M in H2O, 40 mL, 160 mmol) was stirred and heated to 80° C. for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was separated and extracted with hydrochloric acid (2N). The aqueous layer was concentrated under reduced pressure to afford 1-(benzyloxy)but-3-en-2-amine hydrochloride. MS ESI calc'd. for C11H16NO [M+H]+ 178. found 178. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (s, 2H), 7.37-7.28 (m, 5H), 5.89-5.80 (m, 1H), 5.44-5.32 (m, 2H), 4.57-4.50 (m, 2H), 3.99 (s, 1H), 3.62-3.55 (m, 2H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with ethyl acetate
customThe organic layer was separated
extractionextracted with hydrochloric acid (2N)
concentrationThe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-cfa7854ff5cf46228c219b7efc94e6d1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

Loading…