Diethyl Ether → 3-(1-Phenylmethyl-2-pyrrolidinyl)phenyl 2-(4-morpholinyl)ethylcarbamate

HRID 233052Notes

Reaction equation

HRID 233052 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[C:29](=O)(O)[O-:30].[Na+].CCOCC>O1CCCC1.C(O)(=O)C>[N:23]1([CH2:22][CH2:21][NH:20][C:29](=[O:30])[O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][N:8]3[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:14]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 233612863-(1-Phenylmethyl-2-pyrrolidinyl)phenol

Product 1

HCID 233613073-(1-Phenylmethyl-2-pyrrolidinyl)phenyl 2-(4-morpholinyl)ethylcarbamateYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[1-phenylmethyl-2-pyrrolidinyl]phenol (0.64 g) in dry tetrahydrofuran (20 ml) was added 1,1-carbonyldiimidazole (0.61 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 48 hrs, glacial acetic acid (0.50 ml) was added followed by a solution of 4-(2-aminoethyl)morpholine (0.43 ml) in tetrahydrofuran (1.0 ml) and glacial acetic acid (0.20 ml). After 3 hrs, the reaction mixture was poured into saturated sodium bicarbonate solution and ether. The layers were separated, and the aqueous phase was extracted with ether (2 times). The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by radial chromatography, using ether as the eluent. The appropriate fractions were collected and concentrated to give 0.56 g (54%) of product. Recrystallization from ether/petroleum ether gave the analytical sample, mp 74°-77° C.

Workup

  1. waitAfter 3 hrs
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ether (2 times)
  4. washThe combined organic extracts were washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by radial chromatography
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b28dd902fde54c98b3aba4d870242860
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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