Diethyl Ether → HCID 20342206, compound

HRID 66102Notes

Reaction equation

HRID 66102 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)

Sources & evidence

ORD record
ord-512d34e1cbff4098b3384e965c97c799
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Reaction notes

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