Diethyl Ether → HCID 70466639, compound

HRID 1380073Notes

Reaction equation

HRID 1380073 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[C:14]1([CH2:24][C:25]([OH:27])=O)[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([OH:23])=O.S(Cl)([Cl:30])=O.CCO[CH2:35][CH3:36]>C(Cl)Cl>[ClH:30].[ClH:30].[CH3:1][N:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[N:9]1[CH2:36][CH2:35][CH2:11][CH2:10]1)[C:25](=[O:27])[CH2:24][C:14]1[C:15]([CH2:20][C:21]([N:2]([CH3:1])[C@@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:23])=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24123o-Phenylenediacetic acidHCID 24386Thionyl ChlorideHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Product 1

HCID 70466639HCID 70466639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine (0.365 g) was dissolved in methylene chloride (10 ml) and stirred at room temperature. The di-acid chloride of ortho-phenylenediacetic acid (prepared by the action of thionyl chloride on ortho-phenylenediacetic acid, 0.194 g) dissolved in methylene chloride (10 ml) was added and let stand for 0.5 hour. Ether was added to rapidly stirred solution until no more precipitate appeared. After further rapid stirring for one hour, the precipitate was filtered and dried in a vacuum oven at 90° C. for one hour and stored in a predried bottle. The product was in the form of a white solid (400 mg), mp 261°-263° C.

Workup

  1. additionwas added
  2. stirringAfter further rapid stirring for one hour
  3. filtrationthe precipitate was filtered
  4. customdried in a vacuum oven at 90° C. for one hour

Sources & evidence

ORD record
ord-778be1a5cf6d4afaa419029cdae7d914
Source dataset
uspto-grants-1986_04
Patent number
US04579863

Reaction notes

Loading…