Clenbuterol → HCID 70405389, compound

HRID 1995410Notes

Reaction equation

HRID 1995410 reaction equation
[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([CH:6]([OH:13])[CH2:7][NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][C:3]=1[Cl:17].[C:18]([O:21][C:22](=[O:24])[CH3:23])(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([OH:21])(=[O:20])[CH3:19].[NH2:1][C:2]1[C:3]([Cl:17])=[CH:4][C:5]([CH:6]([OH:13])[CH2:7][N:8]([C:9]([CH3:12])([CH3:10])[CH3:11])[C:22](=[O:24])[CH3:23])=[CH:14][C:15]=1[Cl:16]

Participants

4

Reactant 2

HCID 2783ClenbuterolHCID 7918Acetic Anhydride

Product 1

HCID 70405389HCID 70405389, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture containing 2.5 g of 4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl alcohol, 25 ml of pyridine and 10 ml of acetic anhydride is stirred for three hours and evaporated to dryness in vacuo with heating up to 70° C. The residue is treated with ice, 100 ml of CH2Cl2 and 50 ml of 10% NaOH solution. The CH2Cl2 phase is separated, and the aqueous portion is further extracted with CH2CL2 (2×50 ml). The combined CH2CL2 solutions are dried (Na2SO4) and evaporated to dryness to afford a solid after scratching. The solid is washed with hexane and collected to afford 2.61 g of the title compound, mp 126°-136° C.

Workup

  1. customevaporated to dryness in vacuo
  2. additionThe residue is treated with ice, 100 ml of CH2Cl2 and 50 ml of 10% NaOH solution
  3. customThe CH2Cl2 phase is separated
  4. extractionthe aqueous portion is further extracted with CH2CL2 (2×50 ml)
  5. dry with materialThe combined CH2CL2 solutions are dried (Na2SO4)
  6. customevaporated to dryness
  7. customto afford a solid
  8. washThe solid is washed with hexane
  9. customcollected

Sources & evidence

ORD record
ord-d8c82e9b16624c6f8361bebf94b2c35e
Source dataset
uspto-grants-1983_09
Patent number
US04404222

Reaction notes

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