HCID 53857755, compound → HCID 54220615, compound

HRID 2226929Notes

Reaction equation

C(O[C:4]([CH:6]1[CH2:19][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])C>C(N)CC>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[NH:10][C:9]3[CH2:19][CH:6]([C:4]([NH:10][CH2:9][CH2:8][CH3:7])=[O:5])[CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1,2,3,4-Tetrahydro-7-methoxycyclopent[b]indol-2-carboxylic acid ethyl ester (9.5 g, 0.037 mole) was added to n-propyl amine (30 ml) in a sealed tube and heated to 100° C. with stirring for 26 hours. The mixture was then concentrated to yield a brown oil (12.4 g), which was eluted with 10% ethyl acetate in CH2Cl2 and then with 50% ethyl acetate in CH2Cl2 on a silica gel column via HPLC. The desired fractions were concentrated to yield the product as a tan solid 6.5 g, mp 141°-143° C. A portion of this material (1.2 g) was recrystallized from ether in ethyl acetate (5:1) to yield the product as a white solid, 0.8 g, mp 141°-143° C.

Workup

concentrationThe mixture was then concentrated

Sources & evidence

ORD record: ord-d220139994564de5afcba732b3ecb7c2
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05350762

Reaction notes

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