Water → 2-Chloro-5-iodo-N-[(4-methoxyphenyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 1765542Notes

Reaction equation

HRID 1765542 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:9]=1[C:10]([NH:12][CH2:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)=[O:11].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=1.O>O1CCCC1>[Cl:7][C:8]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:9]=1[C:10]([N:12]([CH2:35][C:34]1[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1)[CH2:13][C:14]12[CH2:23][CH:18]3[CH2:17][CH:16]([CH2:22][CH:20]([CH2:19]3)[CH2:21]1)[CH2:15]2)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 699934-Methyloxybenzyl chlorideHCID 120853472-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 211074122-Chloro-5-iodo-N-[(4-methoxyphenyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (18.8 g) was added to a stirred solution of 2-chloro-5-iodo-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)benzamide (prepared as described in WO 99/29661) (60.0 g) in anhydrous tetrahydrofuran (600 mL) at 20° C. under nitrogen. After the addition was complete, 4-methoxybenzyl chloride (20.8 mL) was added. The mixture was heated to reflux for 12 hours and then cooled to room temperature. Water (600 mL) was added and the mixture extracted with dichloromethane (1.2 L then 400 mL). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 12 hours
  4. extractionthe mixture extracted with dichloromethane (1.2 L
  5. dry with materialOrganic extracts were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fc1b42892cd343b49bdfcb718376860a
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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