Acetic Acid → HCID 68749600, compound

HRID 1864785Notes

Reaction equation

HRID 1864785 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]3)=[CH:22][C:21]=1[CH:35]=O.[CH3:37][N:38]1[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40][CH2:39]1>ClCCCl.ClCCl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]3)=[CH:22][C:21]=1[CH2:35][NH:44][CH:41]1[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 27375314-Amino-1-methylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86616466HCID 86616466, compound

Product 1

HCID 68749600HCID 68749600, compoundYield 117.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (400 mg, 1.88 mmol) and then enough acetic acid to bring the pH to 5 were added to a solution of 5-(4-fluoro-3-formylphenyl)-1H-indole (150 mg, 0.63 mmol) and 1-methyl-piperidin-4-ylamine (144 mg, 1.23 mmol) in 15 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane and washed with water. The aqueous phase extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated to leave the crude product, which was eluted through an SCX cation exchange column (elution with methanol, followed by 2M ammonia in methanol) to give 250 mg of product.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave the crude product, which
  7. washwas eluted through an SCX cation exchange column (elution with methanol, followed by 2M ammonia in methanol)

Sources & evidence

ORD record
ord-92c4b589525741d8b90a84ee14d02bc8
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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