Triethylamine → 4-(3-Chloropropionyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

HRID 1605267Notes

Reaction equation

HRID 1605267 reaction equation
[NH:1]1[C:11]2[C:12]3[C:3]([CH2:4][NH:5][CH2:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:2]1.C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][C:23](Cl)=[O:24].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:20][CH2:21][CH2:22][C:23]([N:5]1[CH2:4][C:3]2=[CH:2][NH:1][C:11]3[C:12]2=[C:7]([CH:8]=[CH:9][CH:10]=3)[CH2:6]1)=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 516892Sodium BicarbonateHCID 3041097HCID 3041097, compound

Product 1

HCID 215467344-(3-Chloropropionyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline (3.24 g), described in Example 5, in chloroform (350 ml), triethylamine (6.0 ml) is added, followed by dropwise addition of 3-chloropropionyl chloride (4.2 ml). The mixture is stirred at room temperature for 2.5 hr. Aqueous sodium bicarbonate is added and the stirring is continued for 15 minutes. The layers are separated and the organic phase washed with water, dried and concentrated to give 4-(3-chloropropionyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline, mp 158°-161°C after recrystallizaton from chloroform.

Workup

  1. waitthe stirring is continued for 15 minutes
  2. customThe layers are separated
  3. washthe organic phase washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-68408efb71074f08b1f51e98139aa589
Source dataset
uspto-grants-1976_04
Patent number
US03950343

Reaction notes

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