Chloroform → HCID 86635012, compound
Reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][NH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(Cl)(Cl)[Cl:21].[Cl:24][C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>O>[ClH:21].[CH3:10][N:11]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:25]([Cl:24])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
With cooling with ice, N,N-diisopropylethylamine (10.6 mL) and N-methyl-2-piperidin-1-ylethanamine (7.10 g) were added in that order to chloroform (140 mL) solution of triphosgene (8.15 g). The reaction liquid was stirred for 1 hour with cooling with ice, and then water (25 mL) was added thereto. The reaction liquid was azeotroped with toluene and then dried overnight under reduced pressure to obtain methyl(2-piperidin-1-ylethyl)carbamyl chloride monohydrochloride (20.0 g) as a pale yellow oily substance. Not further purified, the compound was used in the next reaction. Chloroform (2.0 mL), N,N-diisopropylethylamine (0.342 mL), 7H-spiro[furo[3,4-b]pyridine-5,4′-piperidin]-7-one dihydrochloride (136 mg) were added to the obtained methyl(2-piperidin-1-ylethyl)carbamyl chloride monohydrochloride (100 mg), and stirred at 70° C. for 11 hours. The reaction liquid was concentrated under reduced pressure, and then purified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=5% to 50%, gradient) to obtain the entitled compound (57 mg, 24%) as a pale yellow oily substance.
Workup
- customThe reaction liquid
- temperaturewith cooling with ice
- customThe reaction liquid
- customwas azeotroped with toluene
- customdried overnight under reduced pressure
Sources & evidence
- ORD record
- ord-d5cc07bdc4c447ed9126cb4b7b9f6f1e
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158791B2
Reaction notes
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