Diisopropylethylamine → HCID 69592927, compound

HRID 1822984Notes

Reaction equation

HRID 1822984 reaction equation
[S:1]1[C:5]2[C:6]([SH:10])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:11]([N:18]([CH3:29])[CH2:19][CH2:20][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)CC)(C)C>C(#N)CC>[S:1]1[C:5]2[C:6]([S:10][CH:19]([N:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:29])[CH2:20][CH2:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 15678556(R,S)-N-Methyl 3-benzylamino-1-phenyl-1-propanolHCID 17953820HCID 17953820, compound

Product 1

HCID 69592927HCID 69592927, compound

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A solution of 1-benzothiophene-7-thiol (0.32 g, 1.96 mmol), 3-[benzyl(methyl)amino]-1-phenyl-1-propanol (0.5 g, 1.96 mmol), (cyanomethyl) trimethylphosphonium iodide (Ref Tetrahedron, 2001, 57, 5451–5454) (0.714 g, 2.94 mmol), diisopropylethylamine (0.379 g, 2.94 mmol) in propionitrile (5 mL) was stirred at 90° C. in a reacti-vial for 72 h. After this time the reaction was allowed to cool to room temperature. The reaction mixture was purified by an SCX-2 column eluting with methanol followed by ammonia:methanol solution (7 N). The organics were then evaporated and the compound taken directly onto the next step without any further purification LCMS determined successful product formation (M+H+1 [404]).

Workup

  1. customThe reaction mixture was purified by an SCX-2 column
  2. washeluting with methanol
  3. customThe organics were then evaporated
  4. customthe compound taken directly onto the next step without any further purification LCMS

Sources & evidence

ORD record
ord-b45a134a6a6c4864bd7632de7c7b286a
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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