2,5-Dimethoxytetrahydrofuran → HCID 19040628, compound

HRID 1683771Notes

Reaction equation

HRID 1683771 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]([CH2:14][NH2:15])=[CH:4][CH:3]=1.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>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]([CH2:14][N:15]2[CH:18]=[CH:22][CH:21]=[CH:20]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 19040647HCID 19040647, compound

Product 1

HCID 19040628HCID 19040628, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-methanamine (0.75 g, 3.4 mmol) in acetic acid (6.5 ml) was treated with 2,5-dimethoxy-tetrahydrofuran (0.44 ml, 3.4 mmol) and heated to 115° C. for 1 hour. The mixture was quenched with ice water, basified with 20% sodium hydroxide and extracted with ethyl acetate. The organic phase was washed, dried and concentrated. The residue was triturated with ethyl ether and the residue chromatographed on silica gel eluted with methanol-methylene chloride (3:97) to give 6-chloro-2,3,4,5-tetrahydro-3-methyl-9-(1H-pyrrol-1-ylmethyl)-1H-3-benzazepine hydrochloride; mp 219°-223° C.

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was triturated with ethyl ether
  7. customthe residue chromatographed on silica gel
  8. washeluted with methanol-methylene chloride (3:97)

Sources & evidence

ORD record
ord-b5e025cb498c495c88dce310d855a39e
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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