Trifluoroacetic acid → HCID 58591578, compound

HRID 746628Notes

Reaction equation

HRID 746628 reaction equation
[BH4-].[Na+].C(O)(C(F)(F)F)=O.[CH3:10][N:11]([CH3:28])[CH2:12][CH2:13][C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]=1[C:23](=O)[CH2:24][O:25][CH3:26].[NH4+].[OH-]>ClCCl>[CH3:26][O:25][CH2:24][CH2:23][C:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[S:18][C:14]=1[CH2:13][CH2:12][N:11]([CH3:10])[CH3:28]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydride2×HCID 58591559HCID 58591559, compound

Product 1

HCID 58591578HCID 58591578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (16 mg, 0.42 mmol) was added to a cooled (0° C.) solution of TFA (0.6 mL). The mixture was stirred for 30 min at room temperature. A solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-2-methoxy-ethanone (10 mg, 0.036 mmol) in dichloromethane ((0.6 mL) was added and the mixture was heated at reflux for 1 hour. An additional batch of sodium borohydride (10 mg) was added and the reaction was stirred overnight at rt. Diluted NH4OH was added until the pH of the mixture was approximately 9. The product was extracted with dichloromethane, the organic layer was concentrated and purified by mass triggered preparative HPLC to afford {2-[3-(2-methoxy-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amine (Compound 22-2). (MH+=263.9, tR=4.07, Method 2).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. stirringthe reaction was stirred overnight at rt
  4. extractionThe product was extracted with dichloromethane
  5. concentrationthe organic layer was concentrated
  6. custompurified by mass

Sources & evidence

ORD record
ord-ed2b2a0635d446ef8399bb1564ab4c8a
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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