Water → HCID 15132168, compound

HRID 982311Notes

Reaction equation

HRID 982311 reaction equation
[OH:1][C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][C@H:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[H-].[Na+].Cl[C:24]1[N:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:27]=[N:26][N:25]=1.O>CN(C=O)C>[CH3:12][N:9]1[CH2:8][C@H:7]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:6]2[CH:19]=[C:2]([O:1][C:24]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:27]=[N:26][N:25]=3)[C:3]([CH3:20])=[CH:4][C:5]=2[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 10400793HCID 10400793, compound

Product 1

HCID 15132168HCID 15132168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(R)-8-Hydroxy-3,7-dimethyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (13.35g, 0.0499 mol) was dissolved in DMF (70 ml) and 50% sodium hydride in mineral oil (2.4 g, 0.0499 mol) was added with stirring under nitrogen. The solution was stirred at room temperature for one hour longer. A solution of 5-chloro-1-phenyl-1H-tetrazole (9.90 g) in DMF (40 ml) was added dropwise to the solution with stirring. The solution was stirred for two hours longer and then at 45° C. for another 0.5 hour. The solution was chilled and poured into 900 ml of ice and H2O. The solution was extracted with 2× 250 ml of ether. The combined ethyl layers were washed with 300 ml of water. The ether solution was dried and reduced to about 125 ml. The solid was filtered off, m.p. 140°-142° C.

Workup

  1. stirringThe solution was stirred at room temperature for one hour longer
  2. stirringwith stirring
  3. stirringThe solution was stirred for two hours longer
  4. temperatureThe solution was chilled
  5. extractionThe solution was extracted with 2× 250 ml of ether
  6. washThe combined ethyl layers were washed with 300 ml of water
  7. dry with materialThe ether solution was dried
  8. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-661cf2a6db274ac99ad53d56569d3716
Source dataset
uspto-grants-1991_02
Patent number
US04996202

Reaction notes

Loading…