Diethylethanolamine → beta-N-N-diethylaminoethyl-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate

HRID 329331Notes

Reaction equation

[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].C(N(C)CCO)C.[O:16]=[C:17]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]([CH3:37])[C:29](OCCN(C)C)=[O:30])=[CH:27][C:22]=2[CH:21]=[CH:20][C:19]2[CH:38]=[CH:39][CH:40]=[CH:41][C:18]1=2>>[CH2:1]([N:3]([CH2:4][CH2:5][O:6][C:29](=[O:30])[CH:28]([C:26]1[CH:25]=[CH:24][C:23]2[C:17](=[O:16])[C:18]3[CH:41]=[CH:40][CH:39]=[CH:38][C:19]=3[CH:20]=[CH:21][C:22]=2[CH:27]=1)[CH3:37])[CH2:7][CH3:8])[CH3:2]

Participants

Reactant 3

HCID 7497Diethylethanolamine

HCID 17916N-Ethyl-N-methylethanolamine

HCID 12398827HCID 12398827, compound

Product 1

HCID 12398842beta-N-N-diethylaminoethyl-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate

Procedure

In similar manner substituting diethylethanolamine and N-ethyl-N-methylethanolamine for the dimethylethanolamine, there is obtained β-N-N-diethylaminoethyl-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate as an oil (hydrochloride salt: m.p. 117°-123° C; see Example XIV) and β-N-ethyl-N-methylaminoethyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)-propionate [an oil; n.m.r. spectrum in deuterochloroform relative to tetramethylsilane: 0.94 (triplet, CH2CH3); 1.53 (doublet, CHCH3); 2.08 (singlet, N--CH3); 4.17 (triplet, OCH2) and 7.03 ppm (singlet, 10H,11H); mass spectrum: 363 (M+), 305, 233, 205].

Sources & evidence

ORD record: ord-539ff5670e564f4286e8b1c3c4675632
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04020094

Reaction notes

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