Hydrochloric Acid → HCID 20353199, compound

HRID 372102Notes

Reaction equation

HRID 372102 reaction equation
N[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:28].[Na+].[ClH:31]>O>[ClH:31].[OH:28][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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20353202HCID 20353202, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20353199HCID 20353199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.0 g (14.5 mmoles) of 5-amino-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, the product of Example 64, in 50 ml of 1N aqueous hydrochloric acid, cooled to 0°, was added dropwise a solution of 1.0 g (14.5 mmoles) of sodium nitrite in 5 ml of water. The reaction mixture was stirred overnight at room temperature, filtered and then heated to 90°. A precipitate of 5-hydroxy-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole hydrochloride was collected by filtration, m.p. 218-229°; nmr spectrum of free base: δ 1.0-4.0 (m, 19); 6.3-6.7 (m, 2); 6.7-7.2 (m, 5); 8.7 (s, 1).

Workup

  1. filtrationfiltered
  2. temperatureheated to 90°
  3. filtrationA precipitate of 5-hydroxy-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole hydrochloride was collected by filtration, m.p. 218-229°

Sources & evidence

ORD record
ord-61b5c9d506fe41228992d8a101f9535e
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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