Sodium Hydroxide → HCID 20353209, compound

HRID 372106Notes

Reaction equation

HRID 372106 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1.N([O-])=O.[Na+].[N-:31]=[N+:32]=[N-].[Na+].[OH-].[Na+]>Cl.O.C(Cl)Cl>[N:1]([C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:14][CH2:15][CH2:16][CH2:17]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1)=[N+:31]=[N-:32]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 20353202HCID 20353202, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20353209HCID 20353209, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.5 g (0.019 mole) of 5-amino-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole (Example 64) in 5ml of conc. hydrochloric acid and 120 ml of water, cooled to 0°, was added an ice cold solution of 1.5 g (.022 mole) of sodium nitrite in 5 ml of water over a 5 minute period. After stirring 10 minutes at 0°, an ice cold solution of 1.4 g (.022 mole) of sodium azide in 5 ml of water was added portionwise. A cream-colored precipitate formed followed by copious evolution of nitrogen. Stirring was continued for 1 hour at 0°. The reaction mixture was made basic (pH 13) with sodium hydroxide and allowed to stand overnight. It was dissolved in methylene chloride, the organic layer was separated, washed with water and dried over potassium carbonate. Evaporation of the solvent gave 4 g of the crude azide as a deep red oil. It was purified by chromatography on silica gel (5% methanol-chloroform) to give 5-azido-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole; ir spectrum: strong --N=N=N absorption at 2100 cm-1.

Workup

  1. customA cream-colored precipitate formed
  2. stirringStirring
  3. waitwas continued for 1 hour at 0°
  4. waitto stand overnight
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over potassium carbonate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ce1617673dc345d5be146eaac9c907d9
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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