Sodium Hydroxide → 7-Azidoketanserin

HRID 978456Notes

Reaction equation

HRID 978456 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21](=[O:29])[C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:35]=[N+:36]=[N-].[Na+].[OH-].[Na+]>O.C(O)(=O)C>[N:1]([C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH:18]([C:21](=[O:29])[C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH2:19][CH2:20]3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1)=[N+:35]=[N-:36]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 128198HCID 128198, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 30356277-AzidoketanserinYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred and cooled (5° C.) solution of 0.205 parts of 7-amino-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione in 50 parts of an acetic acid solution 1N was added a solution of 0.1725 parts of sodium nitrite in 2 parts of water. The whole was stirred for 20 minutes at 5° C. A solution of 0.1625 parts of sodium azide in 2 parts of water was added and stirring was continued for 20 minutes at 5° C. in vacuo. 5.5 Parts of a sodium hydroxide solution 10N were added whereupon the product solidified. The product was filtered off and crystallized from acetonitrile. The product was filtered off and dried, yielding 0.120 parts (55%) of 7-azido-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)quinazolinedione; mp. 193.7° C. (28).

Workup

  1. stirringThe whole was stirred for 20 minutes at 5° C
  2. stirringstirring
  3. filtrationThe product was filtered off
  4. customcrystallized from acetonitrile
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-311650ab575744d1956773365728897d
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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