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Benzyl Alcohol → Phenylmethyl [3-[(3,4-dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

HRID 1946477
Notes
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Reaction equation

HRID 1946477 reaction equation
N.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][N:11]2[C:15]3[CH:16]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[N:13]=[C:12]2[CH:25]([CH3:27])[CH3:26])[CH:6]=[CH:7][C:8]=1[Cl:9].[CH2:28](O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][N:11]2[C:15]3[CH:16]([CH2:21][C:22]([O:24][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[N:13]=[C:12]2[CH:25]([CH3:27])[CH3:26])[CH:6]=[CH:7][C:8]=1[Cl:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67435460[3-[(3,4-Dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetic acid ammonia salt

Product 1

HCID 58460204Phenylmethyl [3-[(3,4-dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of Example 3 (180 mg) in dichloromethane (5 mL) at 0° C. was added benzyl alcohol (0.095 mL), 4-dimethylamino pyridine (10 mg) and N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (100 mg) sequentially. The reaction was stirred at 0° C. under an atmosphere for 1.5 hr. The reaction was allowed to achieve ambient temperature and stirred for a further 18 hr. The reaction mixture was partitioned between dichloromethane (10 mL) and water (10 mL). The aqueous phase was back extracted with dichloromethane (10 mL). The combined organics were dried (hydrophobic frit) and concentrated in vacuo to give 274 mg of product. The sample was purified on silica using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (159 mg). LC/MS MH+ 485, 487, Rt 2.28 min (5 minute run).

Workup

  1. customto achieve ambient temperature
  2. stirringstirred for a further 18 hr
  3. customThe reaction mixture was partitioned between dichloromethane (10 mL) and water (10 mL)
  4. extractionThe aqueous phase was back extracted with dichloromethane (10 mL)
  5. customThe combined organics were dried (hydrophobic frit)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-320cb40bd3e14c198b1bb0a57a0299bc
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399444B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes