Hydrochloric Acid → HCID 131729849, compound

HRID 2362771Notes

Reaction equation

HRID 2362771 reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][N:42]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)=[C:34]([O:48][CH2:49][CH2:50][CH2:51][N:52]4[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]4)[CH:33]=3)[CH:15]=[CH:16][C:17]=2[O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCOCC>C(O)C>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[N:2]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][N:42]4[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]4)=[C:34]([O:48][CH2:49][CH2:50][CH2:51][N:52]4[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]4)[CH:33]=3)[CH:15]=[CH:16][C:17]=2[O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58000800HCID 58000800, compound

Product 1

HCID 131729849HCID 131729849, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To all ice cooled (0-5° C.) solution of aqueous concentrated HCl (7.0 mL, of 11 N, 77 mmol, 24 equiv.) in 95% ethanol (21 mL) was added dropwise a solution of 1,4-bis{3,4-bis[3-(piperidin-1-yl)propoxy]phenyl}-butane (2.50 g, 3.225 mmol) in 95% ethanol (21 mL)*. The solution was allowed to stir at 0-5° C. for three hours and the solvent was removed on a rotary evaporator keeping the temperature of the water bath at 45° C. The hydrochloride salt was dried under high vacuum for 48 hours. The crude product was then crystallized from ethanol:ether to give 2.46 g of the product (83.2% yield) after drying high vacuum for 72 hours. *Note that the starting material 1,4-bis{3,4-bis[3(piperidin-1-yl)propoxy]phenyl}-butane did not dissolve completely in 95% ethanol at room temperature, so the mixture was heated at 45° C. during which 1,4-bis{3,4-bis[3-(piperidin-1-yl)propoxy]phenyl}-butane dissolved. The solution was cooled to room temperature and added, to the ethanolic HCl solution.

Workup

  1. customthe solvent was removed on a rotary evaporator
  2. customat 45° C
  3. dry with materialThe hydrochloride salt was dried under high vacuum for 48 hours
  4. customThe crude product was then crystallized from ethanol

Sources & evidence

ORD record
ord-f28a225b78914b56aeaba5157010f998
Source dataset
uspto-grants-2014_04
Patent number
US08691845B2

Reaction notes

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