4-(1-Pyrrolidinyl)piperidine → HCID 10434497, compound

HRID 2376849Notes

Reaction equation

HRID 2376849 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:21]([C:31](OC4C=CC=CC=4)=[O:32])C(=O)OC4C=CC=CC=4)[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4].[N:40]1([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH2:44][CH2:43][CH2:42][CH2:41]1>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:31]([N:48]4[CH2:49][CH2:50][CH:45]([N:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[CH2:46][CH2:47]4)=[O:32])[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 21949175Phenyl N-(4-(1-(methylamino)carbonyl-1H-5-indolyloxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate

Product 1

HCID 10434497HCID 10434497, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl N-(4-(1-(methylamino)carbonyl-1H-5-indolyloxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate (12.1 g, 23.2 mmol) synthesized in Production example 5-2 was dissolved in dimethylformamide (150 ml); 4-(1-pyrrolidinyl)piperidine (14.4 g, 93.3 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine and concentrated to about 100 ml. The residue was allowed to be kept cool at 5° C. for overnight to precipitate crystals. The crystals were filtered off, washed with ethyl acetate to yield the title compound (7.8 g, 16.9 mmol, 73%) as white crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated to about 100 ml
  4. temperatureto be kept cool at 5° C. for overnight
  5. customto precipitate crystals
  6. filtrationThe crystals were filtered off
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0664994b171f4dba866b55103132eb4b
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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