4-Chlorobenzylamine → HCID 69731216, compound

HRID 411195Notes

Reaction equation

HRID 411195 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[C:16]2[CH:17]=[CH:18][S:19][C:15]=2[CH:14]=[CH:13][C:12]=1[C:20](OC)=[O:21]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:20]([C:12]2[CH:13]=[CH:14][C:15]3[S:19][CH:18]=[CH:17][C:16]=3[C:11]=2[OH:10])=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 660364-ChlorobenzylamineHCID 22397191Methyl 4-hydroxybenzo[b]thiophene-5-carboxylate

Product 1

HCID 69731216HCID 69731216, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chlorobenzylamine (1 mL) and methyl 4-hydroxy-1-benzothiophene-5-carboxylate (Preparation 13, 0.50 g) is heated to 120° C. under an atmosphere of nitrogen for 4 hours. After cooling, the residue is diluted with ethyl acetate and methanol (1:1) and absorbed onto silica gel. Chromatography on a Biotage column eluting with 500 mL of toluene gave 520 mg (68%) of the title compound as a white solid. Physical characteristics: Mp 168-169° C.; MS (ESI−) m/z 316.1 (M−H)−. Anal. Found: C, 60.82; H, 3.87; N, 4.33.

Workup

  1. temperatureAfter cooling
  2. customabsorbed onto silica gel
  3. washChromatography on a Biotage column eluting with 500 mL of toluene

Sources & evidence

ORD record
ord-eac79477f1164fda88974ce7dea05fae
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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