Dimethylformamide → HCID 86601726, compound

HRID 1784429Notes

Reaction equation

HRID 1784429 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12](N(C)C)=[CH:13][C:14]3[CH2:20][CH2:19][N:18](C)[CH2:17][CH2:16][C:15]=3[CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:26]([Li])CCC.[CH3:31][N:32]([CH3:35])C=O.[Cl-].[NH4+].[O:38]1CCC[CH2:39]1>>[CH3:35][N:32]([C:20]1([CH3:26])[C:14]2[CH:13]=[CH:12][C:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:39]=[O:38])=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[CH:22][C:15]=2[CH2:16][CH2:17][NH:18][CH2:19]1)[CH3:31]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 57592502HCID 57592502, compoundHCID 178418339Butyllithium

Product 1

HCID 86601726HCID 86601726, compound

Procedure

[8-(4-Bromo-benzenesulfonyl)3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-dimethyl-amine (D28) (1.4 g, 3.4 mmol) was cooled to −78° C. in tetrahydrofuran (20 ml) under an argon atmosphere. n-Butyllithium (1.6 ml, 2.5M) was added dropwise and the mixture stirred for 2 mins. Dimethylformamide (300 mg) was added and the mixture allowed to warm to room temperature then saturated ammonium chloride solution (50 ml) was added and the product extracted with ethyl acetate (2×50 ml). The organic layer was evaporated and chromatography on silica eluting with 0-20% methanol/ethyl acetate afforded the subtitled compound. MH+ 373.

Workup

  1. extractionthe product extracted with ethyl acetate (2×50 ml)
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-6a08549888914b82a2f82521f1f35637
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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