5-Bromo-1-methyl-1H-tetrazole → HCID 20403203, compound

HRID 2164744Notes

Reaction equation

HRID 2164744 reaction equation
[NH2:1][CH2:2][CH:3]([OH:20])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:8]=1.Br[C:22]1[N:26]([CH3:27])[N:25]=[N:24][N:23]=1>C(O)C>[CH3:27][N:26]1[C:22]([NH:1][CH2:2][CH:3]([OH:20])[CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:8]=2)=[N:23][N:24]=[N:25]1

Participants

4

Reactant 2

HCID 127974465-Bromo-1-methyl-1H-tetrazoleHCID 202460151-Amino-4-{3-[(piperidin-1-yl)methyl]phenoxy}butan-2-ol

Product 1

HCID 20403203HCID 20403203, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-amino-4-[3-(1-piperidinylmethyl)phenoxy]-2-butanol (1.39 g) and 5-bromo-1-methyl-1H-tetrazole (0.82 g) in absolute ethanol (10 ml) was heated in an autoclave at 125° for 18 h. The solution was evaporated and the residue dissolved in 1M hydrochloric acid (25 ml). The acidic solution was washed with ethyl acetate, basified with excess sodium carbonate and extracted with ethyl acetate. The extract was dried and evaporated to leave a solid which was triturated with dry diethyl ether to give a white solid (1.0 g). This solid was recrystallised from methyl acetate-light petroleum (b.p. 60°-80°) to give the title compound (0.6 g) as white crystals, m.p. 138°-9°.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in 1M hydrochloric acid (25 ml)
  3. washThe acidic solution was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customThe extract was dried
  6. customevaporated
  7. customto leave a solid which
  8. customwas triturated with dry diethyl ether

Sources & evidence

ORD record
ord-68a4605673704cfebaac9762fb2aff03
Source dataset
uspto-grants-1985_03
Patent number
US04507296

Reaction notes

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