Ammonium Chloride → 3-(3-Quinolyl)-2-Propyn-1-ol Dicyclohexyl Carbamate

HRID 1370018

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.CC(C)([O-])C.[K+].[CH:21]1([N:27]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:28](Cl)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[NH4+].[Cl-]>C1COCC1.CC(OC)(C)C>[CH:21]1([N:27]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:28]([O:14][CH2:13][C:12]#[C:11][C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (1 g, 5.4 mmol) in THF (10 ml) and the solution was cooled to 0° C. Potassium t-butoxide (0.67 g, 5.9 mmol) was then added followed by dicyclohexylcarbamoyl chloride (1.32 g, 5.4 mmol). The mixture was stirred for 2 hours at 0° C. and then allowed to warm up to room temperature over a period of 6 hours by which time the reaction was determined to be complete. The reaction mixture was worked up with MTBE (50 ml) and 10% NH4Cl (25 ml) and the organic layers were concentrated to an oil. The purity compared to the standard was 94% and was used as such. Yield=2 g (95%).

Workup

customTo a dry three-necked round-bottom flask equipped with nitrogen inlet
temperatureto warm up to room temperature over a period of 6 hours by which time the reaction
concentrationthe organic layers were concentrated to an oil

Sources & evidence

ORD record: ord-d210645712bd42a79d7f4d0ab308ae3a
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579986B2

Linked notes

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