Triethylamine → HCID 178483421, compound

HRID 630377Notes

Reaction equation

HRID 630377 reaction equation
[OH:1][C:2]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][CH3:13])[CH2:8][CH2:7]1)=[O:4].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br.C(N(CC)CC)C>>[OH:1][C:2]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 206771,9-DibromononaneHCID 178484861HCID 178484861, compound2×

Product 1

HCID 178483421HCID 178483421, compoundYield 55%

Conditions

Temperature
70 °C

Procedure

Trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5, 0.5 g, 0.001 mol), 1,9-dibromononane (2.9 mL, 0.01 mol) and triethylamine (0.44 mL, 0.003 mol) were mixed together under nitrogen atmosphere and stirred at 70° C. for 94 hours. The reaction mixture was evaporated and purified by column chromatography with silica gel, eluting with chloroform/methanol (from 100 to 4:1) to give the title compound as a brown oil (55%).

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by column chromatography with silica gel
  3. washeluting with chloroform/methanol (from 100 to 4:1)

Sources & evidence

ORD record
ord-16a6ea96441a454c91d59a9fa8193083
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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