Methylamine → Aminotetrahydrocyclopenta[b]indole

HRID 1928575Notes

Reaction equation

HRID 1928575 reaction equation
[CH2:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.C[NH2:14]>>[NH2:14][CH:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 66869719Tetrahydrocyclopent(b)indole

Product 1

HCID 66933239Aminotetrahydrocyclopenta[b]indole

Procedure

In Scheme 2, Step A, the phthalimide group of the tetrahydrocyclopenta[b]indole of formula (2) is cleaved with methylamine to provide an aminotetrahydrocyclopenta[b]indole of formula (3). Preferred conditions use a solvent such as ethanol at a temperature of about 0 to 35° C., for 3 to 24 hours. The resulting by-product is removed by making the pH alkaline and filtering the resultant precipitate. The product is isolated from the filtrate by precipitation with water and 10% NaOH.

Sources & evidence

ORD record
ord-adfb3cd9cc624b0c974098d072d26038
Source dataset
uspto-grants-2012_05
Patent number
US08183388B2

Reaction notes

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