Triethylamine → N-[1-[(3-Methoxycarbonyl-1-tricyclo[3.3.1.13,7]decyl)methyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide hydrochloride

HRID 1820306Notes

Reaction equation

HRID 1820306 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]34[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:24][C:18]([C:26]([O:28][CH3:29])=[O:27])([CH2:19]5)[CH2:17]3)[CH2:23]4)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42]([Cl:44])=[O:43].O.N>C(Cl)Cl.CO>[ClH:44].[CH3:29][O:28][C:26]([C:18]12[CH2:24][CH:22]3[CH2:21][CH:20]([CH2:25][C:16]([CH2:15][N:12]4[CH2:13][CH2:14][CH:9]([N:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=5)[C:42]([C:38]5[O:37][CH:41]=[CH:40][CH:39]=5)=[O:43])[CH2:10][CH2:11]4)([CH2:23]3)[CH2:17]1)[CH2:19]2)=[O:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 12896473Azane;hydrateHCID 23109891Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylate

Product 1

HCID 23109886N-[1-[(3-Methoxycarbonyl-1-tricyclo[3.3.1.13,7]decyl)methyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide hydrochlorideYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

After dissolving methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane-1-carboxylate (0.2248 g, 0.565 mmol) in methylene chloride (5 mL), triethylamine (0.12 g, 1.21 mmol) was added at room temperature. Next, 2-furoyl chloride (0.071 mL, 0.724 mmol) was added dropwise while cooling on ice, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was then subjected to chromatography (100 g Merck Art. 9385, methylene chloride:methanol:ammonia water=98:2:0.1-97:3:0.2) without pretreatment, to obtain the free form of the title compound as a colorless oil (0.2675 g, 0.544 mmol) (96% yield). This was further subjected to hydrochloride salification to obtain the title compound as a white solid (0.2951 g, 0.522 mmol) (96% yield).

Workup

  1. additionwas added at room temperature
  2. temperaturewhile cooling on ice

Sources & evidence

ORD record
ord-1381e538b38946d4b9027c4834b1146f
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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