Sodium Hydroxide → HCID 19040644, compound

HRID 1683770Notes

Reaction equation

HRID 1683770 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([NH2:14])=[CH:4][CH:3]=1.CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1.[OH-].[Na+]>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([N:14]2[CH:17]=[CH:21][CH:20]=[CH:19]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 790982,5-DimethoxytetrahydrofuranHCID 13338332HCID 13338332, compound

Product 1

HCID 19040644HCID 19040644, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-amine (633 mg, 3 mmol) in acetic acid (6 ml) was treated with 2,5-dimethoxytetrahydrofuran (396 mg, 3 mmol) and stirred at 110° C. for 1.5 hours. The mixture was poured into ice, basified with 10% sodium hydroxide and extracted with ethyl acetate. The organic phase was dried, concentrated and treated with hydrogen chloride to give 6-chloro-2,3,4,5-tetrahydro-3-methyl-9-(1H-pyrrol-1-yl)-1H-3-benzazepine hydrochloride (methanol-acetonitrile); mp 262°-264° C.

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. additiontreated with hydrogen chloride

Sources & evidence

ORD record
ord-e272e0a18fd04210b5a286e99cb6be80
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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