Sodium Hydroxide → HCID 68489728, compound

HRID 1046326Notes

Reaction equation

HRID 1046326 reaction equation
[C:1]1([CH2:7][C:8]2[CH:34]=[CH:33][C:11]([O:12][CH2:13][CH2:14][N:15]3[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)[CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][N:15]3[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=4)[CH2:17][CH2:16]3)=[CH:33][CH:34]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68490327methyl 4-[[hexahydro-4-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-1,4-diazepin-1-yl]methyl]benzoate

Product 1

HCID 68489728HCID 68489728, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[[hexahydro-4-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-1,4-diazepin-1-yl]methyl]benzoate (55 mg, 0.12 mmol) in methanol (4 mL) was stirred as a solution of aqueous sodium hydroxide (0.60 mL, 2 M) was added. The reaction was stirred for 17 hours at ambient temperature. The reaction was concentrated under reduced pressure. The residue was diluted with water, adjusted to pH 8 with 1 M aqueous hydrochloric acid, and extracted with butanol. The combined organic layers were concentrated under reduced pressure. Flash chromatography gave 46 mg of 4-[[hexahydro-4-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-1,4-diazepin-1-yl]methyl]benzoic acid; 1H NMR (300 MHz, CD3OD) δ 7.94 (d, 2H), 7.36 (d, 2H), 7.21 (dd, 2H), 7.13 (d, 2H), 7.12 (dd, 1H), 7.07 (d, 2H), 6.82 (d, 2H), 4.08 (t, 2H), 3.82 (s, 2H), 3.75 (s, 2H), 3.05 (t, 2H), 2.99 (m, 4H), 2.81 (m, 2H), 2.80 (m, 2H), 1.88 (m, 2H) ppm.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with butanol
  5. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-291a01a1b91e4112926a50e0f91b0439
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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