Alpha-Ethyltryptamine → 2-Ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid n-propyl ester

HRID 736056Notes

Reaction equation

[CH2:1]([CH:3]([CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[NH2:4])[CH3:2].BrCC(=O)C(OCC)=O.Br[CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH2:31][CH3:32])=[O:28]>>[CH2:30]([O:29][C:27]([C:26]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH:3]([CH2:1][CH3:2])[NH:4][CH:25]=1)=[O:28])[CH2:31][CH3:32]

Participants

Reactant 3

HCID 8367Alpha-Ethyltryptamine

HCID 66144Ethyl bromopyruvate

HCID 115139923-Bromo-2-oxopropionate-1-propyl ester

Product 1

HCID 666399532-Ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid n-propyl ester

Procedure

2-Ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid n-propyl ester was prepared in a manner similar to that described in Example 1A but replacing tryptamine hydrochloride with α-ethyl tryptamine and ethyl 3-bromopyruvate with n-propyl 3-bromopyruvate; MS (ESI): 303 (MH+).

Sources & evidence

ORD record: ord-a26c3103d51040d4b1b297858b8f0884
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595311B2

Reaction notes

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