Water → HCID 131714670, compound

HRID 280169Notes

Reaction equation

HRID 280169 reaction equation
[I-].[Na+].Cl[CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:22]=[CH:21][CH:20]=[CH:19][CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C=O)C>[N:23]([CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:22]=[CH:21][CH:20]=[CH:19][CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[N+:24]=[N-:25]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 33557Sodium AzideHCID 131714669HCID 131714669, compound

Product 1

HCID 131714670HCID 131714670, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Sodium iodide (3 g) is added to a stirred solution of 3-(3-chloropropoxy)-1-(1-piperidinylmethyl)benzocyclobutene (0.87 g) in 12 ml of DMF. The reaction mixture is stirred under nitrogen for 12 hours, sodium azide (1.17 g) is added to this solution followed by water (1.2 ml). The resulting suspension is heated at 75° C. for 5 hours. The reaction mixture is partitioned between water and methylene chloride and the organic layer is separated, washed, dried, filtered and evaporated in vacuo yielding the azide product as an oil.

Workup

  1. customThe reaction mixture is partitioned between water and methylene chloride
  2. customthe organic layer is separated
  3. washwashed
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e7b8d1e843bc4c48be492ec3649aa154
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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