Water → HCID 23458403, compound

HRID 1679998Notes

Reaction equation

C(N[NH:9][CH2:10][CH:11]([OH:28])[CH:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.[OH-].[Na+].O.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[CH2:12]([N:9]([CH2:10][CH:11]([OH:28])[CH:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:34](=[O:35])[CH2:33][Cl:32])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of N-benzylamino-2-hydroxy-3-(2-methoxy-phenoxy)-3-phenyl-propylamine (3.5 g) in CH2Cl2 (60 ml), NaOH (0.6 g) and water (16 ml) were added at 0° C. The whole was cooled to -50° C. and chloroacetyl chloride (1.1 ml) diluted in CH2Cl2 (10 ml) was added dropwise. The organic extracts were combined and washed with a saturated solution of NaCl, drying was carried out over Na2SO4 and the solution was then evaporated to dryness, so obtaining N-benzyl-N-chloroacetyl-2-hydroxy-3-(2-methoxy-phenoxy)-3-phenylpropylamine (4.0 g; yield 93%) as an oil, chromatographically pure, which is used as such.

Workup

additionwas added dropwise
washwashed with a saturated solution of NaCl
customdrying

Sources & evidence

ORD record: ord-d9b2b823359c4ef8b0912ae54159c97a
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04271160

Reaction notes

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