Dicyclohexylcarbodiimide → 1,2-Dihydro-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino) butyryloxy]-1,5,5-trimethyl-3H,5H-thiopyrano[2,3-c][1] benzopyran hydrochloride

HRID 1282861Notes

Reaction equation

HRID 1282861 reaction equation
[OH:1][C:2]1[C:7]2[C:8]3[CH:17]([CH3:18])[CH2:16][CH2:15][S:14][C:9]=3[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=1.[ClH:28].[CH3:29][CH:30]([CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[C:31](O)=[O:32].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:28].[CH3:27][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:19]([C:4]1[CH:3]=[C:2]([O:1][C:31](=[O:32])[CH:30]([CH3:29])[CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[C:7]2[C:8]3[CH:17]([CH3:18])[CH2:16][CH2:15][S:14][C:9]=3[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=1)[CH3:20]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 211526892-Methyl-4-piperidin-1-yl-butyric acid hydrochlorideHCID 215199931,2-dihydro-10-hydroxy-8-(3-methyl-2-octyl)-1,5,5-trimethyl-3H,5H-thiopyrano[2,3-c][1]benzopyran

Product 1

HCID 681321981,2-Dihydro-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino) butyryloxy]-1,5,5-trimethyl-3H,5H-thiopyrano[2,3-c][1] benzopyran hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-dihydro-10-hydroxy-8-(3-methyl-2-octyl)-1,5,5-trimethyl-3H,5H-thiopyrano[2,3-c][1]benzopyran is reacted with 2-methyl-4-piperidinobutyric acid hydrochloride in methylene chloride in the presence of dicyclohexylcarbodiimide, according to the procedure of Example 28, to produce the desired ester.

Sources & evidence

ORD record
ord-c90d5d1cb408408f9c215597224edb30
Source dataset
uspto-grants-1976_08
Patent number
US03972880

Reaction notes

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