Dichloromethane → HCID 131727223, compound

HRID 2374804Notes

Reaction equation

Cl.[CH:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:26])[CH2:24][NH2:25])[CH2:19][CH2:18]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N([CH2:32][CH3:33])CC)C.[CH3:34][C:35]1(C)C[C@@H:36]1[C:38](Cl)=[O:39].Cl[CH2:43]Cl>>[CH:13]1[C:9]2[CH:10]=[CH:11][C:12]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[C:7](=[C:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:26])[CH2:24][NH:25][C:38]([CH2:36][C@H:35]4[CH2:34][C:32]4([CH3:33])[CH3:43])=[O:39])[CH2:21][CH2:22]3)[C:8]=2[CH:16]=[CH:15][CH:14]=1

Participants

Reactant 4

HCID 6344Dichloromethane2×

HCID 8471Triethylamine

HCID 28875814HCID 28875814, compound

HCID 68420335HCID 68420335, compound

Product 1

HCID 131727223HCID 131727223, compound

Procedure

200 mg (0.542 mmol) of 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethanamine hydrochloride was dissolved in 1.5 ml of dichloromethane. 137 mg (1.36 mmol) of triethylamine was added to the obtained solution. Then a solution of 86.1 mg (0.650 mmol) of (S)-2,2-dimethylcyclopropanecarboxylic acid chloride in 0.5 ml of dichloromethane was slowly added to the obtained mixture. After stirring for 1 hour, the obtained mixture was roughly purified by the silica gel chromatography (dichloromethane:methanol=98:2) and then purified by the silica gel chromatography (Chromatorex™ NH, Fuji Silysia Chemical LTD., hexane:ethyl acetate=92:8 to 1:4) to obtain the title compound.

Workup

customthe obtained mixture was roughly purified by the silica gel chromatography (dichloromethane:methanol=98:2)
custompurified by the silica gel chromatography (Chromatorex™ NH, Fuji Silysia Chemical LTD., hexane:ethyl acetate=92:8 to 1:4)

Sources & evidence

ORD record: ord-f860348603454f9bb9cfd6a09f06a8d1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462630B2

Reaction notes

Loading…