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1,1'-Carbonyldiimidazole → 3-(1-Phenylmethyl-2-pyrrolidinyl)phenyl 2-(4-morpholinyl)ethylcarbamate

HRID 1742268
Notes
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Reaction equation

HRID 1742268 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.[C:20]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)(N1C=CN=C1)=[O:21].NCCN1C[CH2:39][O:38][CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C.CCOCC>[N:29]1([CH2:30][CH2:31][NH:27][C:20](=[O:21])[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][CH2:39][O:38][CH2:37][CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 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 3

HCID 176
Acetic Acid
Solvent
2×
HCID 3283Diethyl EtherSolvent
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-0a95d265ee9d4b2890bd0e326fb6e9ef
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05338739

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes