Hydrochloric Acid → N-(4-amino-adamantan-1-ylmethyl)-N-benzyl-2-phenyl-acetamide

HRID 41971Notes

Reaction equation

[CH2:1]([N:8]([CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH:22]3[NH:29]C(=O)O)[CH2:20]1)[CH2:26]2)[C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl.O1CCOCC1>[NH2:29][CH:22]1[CH:23]2[CH2:28][C:19]3([CH2:18][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:9](=[O:17])[CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:26][CH:25]([CH2:27][CH:21]1[CH2:20]3)[CH2:24]2

Participants

Conditions

Temperature: 0 °C

Procedure

In a three-necked flask under nitrogen, 0.49 g of tert-butyl ester of {5-[(benzyl-phenylacetyl-amino)-methyl]adamantan-2-yl}-carbamic acid is dissolved in 1.7 ml of anhydrous dichloromethane. It is cooled to 0° C. and 3.64 ml of 4N solution of hydrochloric acid in dioxane is added. The reaction mixture is stirred for 1 h at room temperature and then concentrated to dryness. 20 ml of water is added, the reaction mixture is basified with potassium carbonate and it is extracted with dichloromethane until exhaustion of the aqueous phase. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated to dryness. 0.35 g of N-(4-amino-adamantan-1-ylmethyl)-N-benzyl-2-phenyl-acetamide is obtained, and is used subsequently as it is.

Workup

concentrationconcentrated to dryness
addition20 ml of water is added
extractionis extracted with dichloromethane until exhaustion of the aqueous phase
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-5ddbc2cb23894613a519bbfa6ef7ef23
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536173B2

Reaction notes

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