3-Butyn-2-amine, 2-methyl- → HCID 87184719, compound

HRID 1422644Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].[CH3:16][C:17]([NH2:21])([C:19]#[CH:20])[CH3:18].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:8][C:6](=[CH2:7])[CH2:5][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:3][CH2:2][NH:21][C:17]([CH3:18])([C:19]#[CH:20])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (550 mg, 2.45 mmol), 1,1-dimethylpropargylamine (204 mg, 2.45 mmol), KI (447 mg, 2.7 mmol), i-Pr2NEt (05 mL, 2.7 mmol) and dry DMF (3 mL) was heated at 80° C. in an oil bath for 24 h. The mixture was concentrated to leave a brown oil which was purified by chromatography on a 12-g silica cartridge eluted with a 0-10% MeOH in CH2Cl2 gradient to afford 5-methyl-1-(2-methylbut-3-yn-2-ylamino)-3-phenylhex-5-en-3-ol (283 mg, 42%) as a brown solid which was used in the next step without further purification. LC-MS Method 1 tR=1.08 min, m/z=272.

Workup

concentrationThe mixture was concentrated
customto leave a brown oil which
customwas purified by chromatography on a 12-g silica cartridge
washeluted with a 0-10% MeOH in CH2Cl2 gradient

Sources & evidence

ORD record: ord-b7539b4573654b51919f689e8001d014
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927539B2

Reaction notes

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