Diethyl Ether → HCID 20342206, compound

HRID 259367Notes

Reaction equation

HRID 259367 reaction equation
[C:1]12([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(OCC)C.C(Cl)[Cl:29]>Cl>[ClH:29].[C:1]12([O:11][C:12]3[CH:13]=[CH:14][C:15]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:16][CH:17]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 6344DichloromethaneHCID 12510310HCID 12510310, compound

Product 1

HCID 20342206HCID 20342206, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 29.8 g (0.100 mole) of N-[4-(1-adamantyloxy)phenyl]pyrrolidine dissolved in CH2Cl2 (200 ml) and diethyl ether (25 ml) stirred and cooled in an ice bath is added in one portion 44 ml of 3.4 N HCl in ether (0.15 mole of HCl). After 30 minutes' stirring, the solvent is evaporated. The resulting solid (33.8 g) is recrystallized from CH2Cl2 (120 ml) - diethyl ether (100 ml) to give 29.0 g of white solid product, mp (in bath at 148°; 1°/minute temperature rise), 163.4°-166.8° C. Nmr, ir, and UV spectra were in accord with the structure.

Workup

  1. temperaturecooled in an ice bath
  2. customthe solvent is evaporated
  3. customThe resulting solid (33.8 g) is recrystallized from CH2Cl2 (120 ml) - diethyl ether (100 ml)

Sources & evidence

ORD record
ord-5acd924b4a084709a0afb6109e5839d2
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

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