Isopropylamine → 2-Formyl-1,2,3,4-tetrahydro-6-(2-hydroxy-3-isopropylamino-propoxy)-isoquinoline

HRID 597209Notes

Reaction equation

HRID 597209 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([CH:15]=[O:16])[CH2:9][CH2:8]2.[CH:18]([NH2:21])([CH3:20])[CH3:19]>C(O)(C)C>[CH:15]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:17][NH:21][CH:18]([CH3:20])[CH3:19])[CH:6]=2)[CH2:11]1)=[O:16]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 214470066-(2,3-Epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 539914442-Formyl-1,2,3,4-tetrahydro-6-(2-hydroxy-3-isopropylamino-propoxy)-isoquinoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

23.3 g. of 6-(2,3-epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinoline are held at the boiling point under reflux with 59.1 g of isopropylamine in 100 ml of isopropanol for 5 hours. The mixture is evaporated and the residue is rubbed with 150 ml of diethyl ether. 27.5 g of 2-formyl-1,2,3,4-tetrahydro-6-(2-hydroxy-3-isopropylamino-propoxy)-isoquinoline are obtained. m.p. = 56.6° - 58° C.

Workup

  1. customThe mixture is evaporated

Sources & evidence

ORD record
ord-8914327ffab041fab43261d8163c7a44
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

Loading…