Formamide → HCID 15491310, compound

HRID 895341Notes

Reaction equation

HRID 895341 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:15][O:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[CH2:10][CH2:9]1)C.C([NH2:41])=O.C[O-].[Na+]>>[F:25][C:24]([F:27])([F:26])[C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([C:28]([F:29])([F:31])[F:30])[CH:21]=1)[CH2:17][O:16][CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][C:4]([NH2:41])=[O:3])[CH2:9][CH2:10]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 10942334Sodium Methoxide2×HCID 86590285HCID 86590285, compound2×

Product 1

HCID 15491310HCID 15491310, compoundYield 86%

Conditions

Temperature
95 °C

Procedure

In a round-bottomed flask fitted with a reflux condenser are introduced 493 mg (0.9 mmoles) of 4-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-butyric acid ethyl ester (compound 138 prepared at example 1.4.1 above), 15 ml of formamide and 97 mg (1.8 mmoles) of sodium methoxide. The mixture is heated to 95° C. for 4 hours, then 48 mg (0.9 mmole) of sodium methoxide are added and the mixture is kept overnight at 85° C. The mixture is cooled and partitioned between diethyl ether (100 ml) and brine (100 ml). The organic phase is dried and volatile substances are removed under reduced pressure, affording 400 mg of 4-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-butyramide as a yellow oil (yield 86%). The dimaleate salt of compound 288 is prepared in 2-butanone (yield: 4.32 g as a white solid).

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. temperatureThe mixture is cooled
  3. custompartitioned between diethyl ether (100 ml) and brine (100 ml)
  4. customThe organic phase is dried
  5. customvolatile substances are removed under reduced pressure

Sources & evidence

ORD record
ord-989475dac1504c3583600c7df2d79c0b
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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